Pure & Appl. Chem., Vol. 68, No. 10, pp. 1919-2008, 1996.
`Printed in Great Britain.
`Q 1996 IUPAC
`
`INTERNATIONAL UNION OF PURE
`AND APPLIED CHEMISTRY
`AND
`INTERNATIONAL UNION OF BIOCHEMISTRY
`AND MOLECULAR BIOLOGY
`JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE*
`NOMENCLATURE OF CARBOHYDRATES
`(Recommendations 1996)
`
`Prepared for publication by
`ALAN D. McNAUGHT
`The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 4WF, UK
`
`*Members of the Commission (JCBN) at various times during the work on this document (1983-1996)
`were as follows:
`Chairmen: H. B. F. Dixon (UK), J. F. G. Vliegenthart (Netherlands), A. Cornish-Bowden (France);
`Secretaries: A. Cornish-Bowden (France), M. A. Chester (Sweden), A. J. Barrett (UK), J. C. Rigg
`(Netherlands); Members: J. R. Bull (RSA), R. Cammack (UK), D. Coucouvanis (USA), D. Horton
`(USA), M. A. C. Kaplan (Brazil), P. Karlson (Germany), C. Li2becq (Belgium), K. L. Loening
`(USA), G. P. Moss (UK), J. Reedijk (Netherlands), K. F. Tipton (Ireland), S. Velick (USA),
`P. Venetianer (Hungary).
`Additional contributors to the formulation of these recommendations:
`Expert Panel: D. Horton (USA) (Convener), 0. Achmatowicz (Poland), L. Anderson (USA), S. J.
`Angyal (Australia), R. Gigg (UK), B. Lindberg (Sweden), D. J. Manners (UK), H. Paulsen
`(Germany), R. Schauer (Germany).
`Nomenclature Committee of IUBMB (NC-IUBMB) (those additional to JCBN): A. Bairoch
`(Switzerland), H. Berman (USA), H. Bielka (Germany), C. R. Cantor (USA), W. Saenger (Germany),
`N. Sharon (Israel), E. van Lenten (USA), E. C. Webb (Australia).
`American Chemical Society Committee for Carbohydrate Nomenclature: D. Horton (Chairman),
`L. Anderson, D. C. Baker, H. H. Baer, J. N. BeMiller, B. Bossenbroek, R. W. Jeanloz, K. L. Loening,
`W. A. Szarek, R. S. Tipson, W. J. Whelan, R. L. Whistler.
`Corresponding Members of the ACS Committee for Carbohydrate Nomenclature (other than JCBN
`and the expert panel): R. F. Brady (USA), J. S. Brimacombe (UK), J. G. Buchanan (UK), B. Coxon
`(USA), J. Defaye (France), N. K. Kochetkov (Russia), R. U. Lemieux (Canada), R. H. Marchessault
`(Canada), J. M. Webber (UK).
`Correspondence on these recommendations should be addressed to Dr Alan D. McNaught at the
`above address or to any member of the Commission.
`
`Republication or reproduction of this report or its storage and/or dissemination by electronic means is permitted
`without the need for formal IUPACpermission on condition that an acknowledgement, with full reference to the
`source along with use of the copyright symbol 0, the name IUPAC and the year of publication are prominently
`visible. Publication of a translation into another language is subject to the additional condition of prior approval
`from the relevant IUPAC National Adhering Organization.
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`
`NOMENCLATURE OF CARBOHYDRATES
`(Recommendations 1996)
`Contents
`
`Preamble
`2-Carb-0. Historical development of carbohydrate nomenclature
`0.1. Early approaches
`0.2. The contribution of Emil Fischer
`0.3. Cyclic forms
`0.4. Nomenclature commissions
`2-Carb-I. Definitions and conventions
`1.1. Carbohydrates
`1.2. Monosaccharides (aldoses and ketoses)
`1.3. Dialdoses
`1.4. Diketoses
`1.5. Ketoaldoses (aldoketoses)
`1.6. Deoxy sugars
`1.7. Amino sugars
`1.8. Alditols
`1.9. Aldonic acids
`1.10. Ketoaldonic acids
`1.1 1. Uronic acids
`1.12. Aldaric acids
`1.13. Glycosides
`1.14. Oligosaccharides
`1.15. Polysaccharides
`1.16. Conventions for examples
`2-Carb-2. Parent monosaccharides
`2.1. Choice of parent structure
`2.2. Numbering and naming of the parent structure
`2-Carb-3. The Fischerprojection of the acyclic form
`2-Carb-4. ConJgurational symbols and prefues
`4.1. Use of D and L
`4.2. The configurational atom
`4.3. Configurational prefixes in systematic names
`4.4. Racemates and meso forms
`4.5. Optical rotation
`2-Carb-5. Cyclic forms and their representation
`5.1. Ring size
`5.2. The Fischer projection
`5.3. Modified Fischer projection
`5.4. The Haworth representation
`5.5. Unconventional Haworth representations
`5.6. The Mills depiction
`5.7. Depiction of conformation
`5.8. Conformations of acyclic chains
`2-Carb-6. Anomeric forms; use of a and p
`6.1. The anomeric centre
`6.2. The anomeric reference atom and the anomeric configurational symbol
`6.3. Mixtures of anomers
`6.4. Use of a and p
`2-Carb-7. Conformation of cyclic forms
`7.1. The conformational descriptor
`7.2. Notation of ring shape
`7.3. Notation of variants
`7.4. Enantiomers
`2-Carb-8. Afdoses
`8.1. Trivial names
`8.2. Systematic names
`8.3. Multiple configurational prefiies
`
`1923
`1923
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`1924
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`1926
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`1928
`1929
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`1930
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`1934
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`1936
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`1938
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`Nomenclature of carbohydrates
`
`1921
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`8.4. Multiple sets of chiral centres
`8.5. Anomeric configuration in cyclic forms of higher aldoses
`2-Carb-9. Dialdoses
`2-Carb-10. Ketoses
`10.1. Classification
`10.2. Trivial names
`10.3. Systematic names
`10.4. Configurational prefixes
`2-Carb-I I . Diketoses
`1 1.1. Systematic names
`11.2. Multiple sets of chiral centres
`2-Curb-12. Ketoaldoses (aldokztoses, aldosuloses)
`12.1. Systematic names
`12.2. Dehydro names
`2-Carb-13. Deoxy sugars
`13.1. Trivial names
`13.2. Names derived from trivial names of sugars
`13.3. Systematic names
`13.4. Deoxy alditols
`2-Carb-14. Amino sugars
`14.1. General principles
`14.2. Trivial names
`14.3. Systematic names
`2-Carb-15. Thio sugars and other chalcogen analogues
`2-Carb-I 6. Other substituted monosaccharides
`16.1. Replacement of hydrogen at a non-terminal carbon atom
`16.2. Replacement of OH at a non-terminal carbon atom
`16.3. Unequal substitution at a non-terminal carbon atom
`16.4. Terminal substitution
`16.5. Replacement of carbonyl oxygen by nitrogen (imines, hydrazones, osazones etc.)
`16.6. Isotopic substitution and isotopic labelling
`2-Carb-I 7. Unsaturated monosaccharides
`17.1. General principles
`17.2. Double bonds
`17.3. Triple bonds and cumulative double bonds
`2-Carb-18. Branched-chain sugars
`18.1. Trivial names
`18.2. Systematic names
`18.3. Choice of parent
`18.4. Naming the branches
`18.5. Numbering
`18.6. Terminal substitution
`2-Carb-19. Alditols
`19.1. Naming
`19.2. meso Forms
`2-Curb-20. Aldonic acids
`20.1. Naming
`20.2. Derivatives
`2-Carb-21. Ketoaldonic acids
`21.1. Naming
`21.3. Derivatives
`2-Curb-22. Uronic ac&
`22.1. Naming and numbering
`22.2. Derivatives
`2-Carb-23. AIdQric acids
`23.1. Naming
`23.2. meso Forms
`23.3. Trivial names
`23.4. Derivatives
`2-Carb-24. 0-Substitution
`24.1. Acyl (alkyl) names
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`1940
`1940
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`1942
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`1943
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`1944
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`1946
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`1947
`1948
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`1951
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`1954
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`1958
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`1959
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`1961
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`1962
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`1964
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`1965
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`24.2. Phosphorus esters
`24.3. Sulfates
`2-Carb-25. N-Substitution
`2-Carb-26. Intramolecular anhydrides
`2-Carb-27. Intermolecular anhydrides
`2-Carb-28. Cyclic acetals
`2-Carb-29. Uemiacetals and hemithioacetals
`2-Carb-30. Acetals, ketals and their thio analogues
`2-Carb-31. Names for monosaccharide residues
`3 1.1. Glycosyl residues
`3 1.2. Monosaccharides as substituent groups
`31.3. Bivalent and tervalent residues
`2-Carb-32. Radicals, cations and anions
`2-Carb-33. Glycosides and glycosyl compounds
`33.1. Definitions
`33.2. Glycosides
`33.3. Thiogly cosides.
`33.4. Selenoglycosides
`33.5. Glycosyl halides
`33.6. N-Glycosyl compounds (glycosylamines)
`33.7. C-Glycosyl compounds
`2-Carb-34. Replacement of ring oxygen by other elements
`34.1. Replacement by nitrogen or phosphorus
`34.2. Replacement by carbon
`2-Carb-35. Carbohydrates containing additional rings
`35.1. Use of bivalent substituent prefixes
`35.2. Ring fusion methods
`35.3. Spiro systems
`2-Carb-36. Disaccharides
`36.1. Definition
`36.2. Disaccharides without a free hemiacetal group
`36.3. Disaccharides with a free hemiacetal group
`36.4. Trivial names
`2-Carb-37. Oligosacchurides
`37.1. Oligosaccharides without a free hemiacetal group
`37.2. Oligosaccharides with a free hemiacetal group
`37.3. Branched oligosaccharides
`37.4. Cyclic oligosaccharides
`37.5. Oligosaccharide analogues
`2-Carb-38. Use of symbols for defining oligosaccharide structures
`38.1. General considerations
`38.2. Representations of sugar chains
`38.3. The extended form
`38.4. The condensed form
`38.5. The short form
`2-Carb-39. Polysacchurides
`39.1. Names for homopolysaccharides
`39.2. Designation of configuration of residues
`39.3. Designation of linkage
`39.4. Naming of newly discovered polysaccharides
`39.5. Uronic acid derivatives.
`39.6. Amino sugar derivatives
`39.7. Polysaccharides composed of more than one kind of residue
`39.8. Substituted residues
`39.9. Glycoproteins, proteoglycans and peptidoglycans
`References
`Appendix
`Trivial Names for Carbohydrates, with their Systematic Equivalents
`Glossary of Glycose-based Terms
`
`1968
`1969
`1970
`1971
`1972
`1973
`1974
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`1976
`1978
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`1984
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`1985
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`1989
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`1991
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`1996
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`1999
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`2003
`2005
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`
`Nomenclature of carbohydrates
`
`1923
`
`Preamble
`These Recommendations expand and replace the Tentative Rules for Carbohydrate Nomenclature [ 11 issued
`in 1969 jointly by the IUPAC Commission on the Nomenclature of Organic Chemistry and the TUB-IUPAC
`Commission on Biochemical Nomenclature (CBN) and reprinted in [2]. They also replace other published
`JCBN Recommendations [3-71 that deal with specialized areas of carbohydrate terminology; however, these
`documents can be consulted for further examples. Of relevance to the field, though not incorporated into the
`present document, are the following recommendations:
`Nomenclature of cyclitols, 1973 [8]
`Numbering of atoms in myo-inositol, 1988 [9]
`Symbols for specifying the conformation of polysaccharide chains, 198 1 [ 101
`Nomenclature of glycoproteins, glycopeptides and peptidoglycans, 1985 [ 1 11
`Nomenclature of glycolipids, in preparation [ 121
`The present Recommendations deal with the acyclic and cyclic forms of monosaccharides and their simple
`derivatives, as well as with the nomenclature of oligosaccharides and polysaccharides. They are additional to
`the Definitive Rules for the Nomenclature of Organic Chemistry [13,14] and are intended to govern those
`aspects of the nomenclature of carbohydrates not covered by those rules.
`2-Curb-0. Historical development of carbohydrate nomenclature [15]
`2-Carb-0.1. Early approaches
`In the early nineteenth century, individual sugars were often named after their source, e.g. grape sugar
`(Traubenzucker) for glucose, cane sugar (Rohrzucker) for saccharose (the name sucrose was coined much
`later). The name glucose was coined in 1838; KekulC in 1866 proposed the name ‘dextrose’ because glucose
`is dextrorotatory, and the laevorotatory ‘fruit sugar’ (Fruchtzucker, fructose) was for some time named
`‘laevulose’ (American spelling ‘levulose’). Very early, consensus was reached that sugars should be named
`with the ending ‘-ose’, and by combination with the French word ‘cellule’ for cell the term cellulose was
`coined, long before the structure was known. The term ‘carbohydrate’ (French ‘hydrate de carbone’) was
`applied originally to monosaccharides, in recognition of the fact that their empirical composition can be
`expressed as Cn(H20)n. However the term is now used generically in a wider sense (see 2-Carb- 1.1).
`2-Carb-0.2. The contribution of Emil Fischer
`Emil Fischer [ 161 began his fundamental studies on carbohydrates in 1880. Within ten years, he could assign
`the relative configurations of most known sugars and had also synthesized many sugars. This led to the
`necessity to name the various compounds. Fischer and others laid the foundations of a terminology still in
`use, based on the terms triose, tetrose, pentose, and hexose. He endorsed Armstrong’s proposal to classify
`sugars into aldoses and ketoses, and proposed the name fructose for laevulose, because he found that the sign
`of optical rotation was not a suitable criterion for grouping sugars into families.
`The concept of stereochemistry, developed since 1874 by van’t Hoff and Le Bel, had a great impact on
`carbohydrate chemistry because it could easily explain isomerism. Emil Fischer introduced the classical
`projection formulae for sugars, with a standard orientation (carbon chain vertical, carbonyl group at the top);
`since he used models with flexible bonds between the atoms, he could easily ‘stretch’ his sugar models into
`a position suitable for projection. He assigned to the dextrorotatory glucose (via the derived glucaric acid)
`the projection with the OH group at C-5 pointing to the right, well knowing that there was a 50% chance that
`this was wrong. Much later (Bijvoet, 1951), it was proved correct in the absolute sense.
`Rosanoff in 1906 selected the enantiomeric glyceraldehydes as the point of reference; any sugar derivable by
`chain lengthening from what is now known as D-glyceraldehyde belongs to the D series, a convention still in
`use.
`2-Carb-0.3. Cyclic forms
`Towards the end of the nineteenth century it was realized that the free sugars (not only the glycosides) existed
`as cyclic hemiacetals or hemiketals. Mutarotation, discovered in 1846 by Dubrunfaut, was now interpreted
`as being due to a change in the configuration of the glycosidic (anomeric) carbon atom. Emil Fischer assumed
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`the cyclic form to be a five-membered ring, which Tollens designated by the symbol <1,4>, while the
`six-membered ring received the symbol < 1,5>.
`In the 1920s, Haworth and his school proposed the terms ‘furanose’ and ‘pyranose’ for the two forms. Haworth
`also introduced the ‘Haworth depiction’ for writing structural formulae, a convention that was soon widely
`followed.
`2-Carb-0.4. Nomenclature commissions
`Up to the 1940s, nomenclature proposals were made by individuals; in some cases they were followed by the
`scientific community and in some cases not. Official bodies like the International Union of Chemistry, though
`developing and expanding the Geneva nomenclature for organic compounds, made little progress with
`carbohydrate nomenclature. The IUPAC Commission on Nomenclature of Biological Chemistry put forward
`a classification scheme for carbohydrates, but the new terms proposed have not survived. However in 1939
`the American Chemical Society (ACS) formed a committee to look into this matter, since rapid progress in
`the field had led to various misnomers arising from the lack of guidelines. Within this committee, the
`foundations of modem systematic nomenclature for carbohydrates and derivatives were laid: numbering of
`the sugar chain, the use of D and L and a and p, and the designation of stereochemistry by italicized prefixes
`(multiple prefixes for longer chains). Some preliminary communications appeared, and the final report,
`prepared by M.L. Wolfrom, was approved by the ACS Council and published in 1948 [17].
`Not all problems were solved, however, and different usages were encountered on the two sides of the Atlantic.
`A joint British-American committee was therefore set up, and in 1952 it published ‘Rules for Carbohydrate
`Nomenclature’ [ 181. This work was continued, and a revised version was endorsed in 1963 by the American
`Chemical Society and by the Chemical Society in Britain and published [19]. The publication of this report
`led the IUPAC Commission on Nomenclature of Organic Chemistry to consider the preparation of a set of
`IUPAC Rules for Carbohydrate Nomenclature. This was done jointly with the IUPAC-TUB Commission on
`Biochemical Nomenclature, and resulted in the ‘Tentative Rules for Carbohydrate Nomenclature, Part I,
`1969’. published in 1971/72 in several journals [l]. It is a revision of this 1971 document that is presented
`here. In the present document, recommendations are designated 2-Carb-n, to distinguish them from the Carb-n
`recommendations in the previous publication.
`2-Carb-I. Definitions and conventions
`2-Carb-1.1. Carbohydrates
`The generic term ‘carbohydrate’ includes monosaccharides, oligosaccharides and polysaccharides as well as
`substances derived from monosaccharides by reduction of the carbonyl group (alditols), by oxidation of one
`or more terminal groups to carboxylic acids, or by replacement of one or more hydroxy group(s) by a hydrogen
`atom, an amino group, a thiol group or similar heteroatomic groups. It also includes derivatives of these
`compounds. The term ‘sugar’ is frequently applied to monosaccharides and lower oligosaccharides. It is
`noteworthy that about 3% of the compounds listed by Chemical Abstracts Service (i.e. more than 360 000)
`are named by the methods of carbohydrate nomenclature.
`Note. Cyclitols are generally not regarded as carbohydrates. Their nomenclature is dealt with in other recommendations
`[8,91.
`2-Carb-1.2. Monosaccharides
`Parent monosaccharides are polyhydroxy aldehydes H-[CHOHIn-CHO or polyhydroxy ketones H-[CHOHIn-
`CO-[CHOHIm-H with three or more carbon atoms.
`The generic term ‘monosaccharide’ (as opposed to oligosaccharide or polysaccharide) denotes a single unit,
`without glycosidic connection to other such units. It includes aldoses, dialdoses, aldoketoses, ketoses and
`diketoses, as well as deoxy sugars and amino sugars, and their derivatives, provided that the parent compound
`has a (potential) carbonyl group.
`1.2. I . Aldoses and ketoses
`Monosaccharides with an aldehydic carbonyl or potential aldehydic carbonyl group are called aldoses; those
`with a ketonic carbonyl or potential ketonic carbonyl group, ketoses.
`Note. The term ‘potential aldehydic carbonyl group’ refers to the hemiacetal group arising from ring closure. Likewise,
`the term ‘potential ketonic carbonyl group’ refers to the hemiketal structure (see 2-Carb-5).
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`
`1.2.2. Cyclic forms
`Cyclic hemiacetals or hemiketals of sugars with a five-membered (tetrahydrofuran) ring are called furanoses,
`those with a six-membered (tetrahydropyran) ring pyranoses. For sugars with other ring sizes see 2-Carb-5.
`2-Carb-1.3. Dialdoses
`Monosaccharides containing two (potential) aldehydic carbonyl groups are called dialdoses (see 2-Carb-9).
`2-Carb-1.4. Diketoses
`Monosaccharides containing two (potential) ketonic carbonyl groups are termed diketoses (see 2-Carb- 1 1).
`2-Carb-1.5. Ketoaldoses (aldoketoses, aldosuloses)
`Monosaccharides containing a (potential) aldehydic group and a (potential) ketonic group are called ketoald-
`oses (see 2-Carb- 12); this term is preferred to the alternatives on the basis of 2-Carb-2.1.1 (aldose preferred
`to ketose).
`2-Carb-1.6. Deoxy sugars
`Monosaccharides in which an alcoholic hydroxy group has been replaced by a hydrogen atom are called deoxy
`sugars (see 2-Carb- 13).
`2-Carb-1.7 Amino sugars
`Monosaccharides in which an alcoholic hydroxy group has been replaced by an amino group are called amino
`sugars (see 2-Carb-14). When the hemiacetal hydroxy group is replaced, the compounds are called glycosyl-
`amines.
`2-Carb-1.8. Alditols
`The polyhydric alcohols arising formally from the replacement of a carbonyl group in a monosaccharide with
`a CHOH group are termed alditols (see 2-Carb-19).
`2-Carb-1.9. Aldonic acids
`Monocarboxylic acids formally derived from aldoses by replacement of the aldehydic group by a carboxy
`group are termed aldonic acids (see 2-Carh-20).
`2-Carb-1.10. Ketoaldonic acids
`0x0 carboxylic acids formally derived from aldonic acids by replacement of a secondary CHOH group by a
`carbonyl group are called ketoaldonic acids (see 2-Carb-2 1).
`2-Carb-1.11. Uronic acids
`Monocarboxylic acids formally derived from aldoses by replacement of the CH2OH group with a carboxy
`group are termed uronic acids (see 2-Carb-22).
`2-Carb-1.12. Aldaric acids
`The dicarboxylic acids formed from aldoses by replacement of both terminal groups (CHO and CH20H) by
`carboxy groups are called aldaric acids (see 2-Carb-23).
`2-Carb-1.13. Glycosides
`Glycosides are mixed acetals formally arising by elimination of water between the hemiacetal or hemiketal
`hydroxy group of a sugar and a hydroxy group of a second compound. The bond between the two components
`is called a glycosidic bond.
`For an extension of this definition, see 2-Carb-33.
`2-Carb-1.14. Oligosaccharides
`Oligosaccharides are compounds in which monosaccharide units are joined by glycosidic linkages. According
`to the number of units, they are called disaccharides, trisaccharides, tetrasaccharides, pentasaccharides etc.
`The borderline with polysaccharides cannot be drawn strictly; however the term ‘oligosaccharide’ is
`commonly used to refer to a defined structure as opposed to a polymer of unspecified length or a homologous
`mixture. When the linkages are of other types, the compounds are regarded as oligosaccharide analogues.
`(See 2-Carb-37.)
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`Note. This definition is broader than that given in [6], to reflect current usage.
`2-Carb-1.15. Polysaccharides
`‘Polysaccharide’ (glycan) is the name given to a macromolecule consisting of a large number of monosac-
`charide (glycose) residues joined to each other by glycosidic linkages. The term poly(g1ycose) is not a full
`synonym for polysaccharide (glycan) (cf. [20]), because it includes macromolecules composed of glycose
`residues joined to each other by non-glycosidic linkages.
`For polysaccharides containing a substantial proportion of amino sugar residues, the term polysaccharide is
`adequate, although the term glycosaminoglycan may be used where particular emphasis is desired.
`Polysaccharides composed of only one lund of monosaccharide are described as homopolysaccharides
`(homoglycans). Similarly, if two or more different kinds of monomeric unit are present, the class name
`heteropolysaccharide (heteroglycan) may be used. (See 2-Cab-39.)
`The term ‘glycan’ has also been used for the saccharide component of a glycoprotein, even though the chain
`length may not be large.
`The term polysaccharide has also been widely used for macromolecules containing glycose or alditol residues
`in which both glycosidic and phosphate diester linkages are present.
`2-Carb-1.16. Conventions for examples
`1.16.1. Names of examples are given with an initial capital letter (e.g. ‘L-glycero-P-D-gluco-Heptopyranose’)
`to clarify the usage in headings and to show which letter controls the ordering in an alphabetical index.
`1.16.2. The following abbreviations are commonly used for substituent groups in structural formulae: Ac
`(acetyl), Bn or PhCH2 (benzyl), Bz or PhCO (benzoyl), Et (ethyl), Me (methyl), Me3Si (not TMS)
`(trimethylsilyl), Bu‘Me2Si (not TBDMS) (rert-butyldimethy lsilyl), Ph (phenyl), Tf (triflyl = trifluoromethane-
`sulfonyl), Ts (tosyl = toluene-p-sulfonyl), Tr (trityl).
`2-Carb-2. Parent monosaccharides
`2-Carb-2.1. Choice of parent structure
`In cases where more than one monosaccharide structure is embedded in a larger molecule, a parent structure
`is chosen on the basis of the following criteria, applied in the order given until a decision is reached:
`2.1.1. The parent that includes the functional group most preferred by general principles of organic
`nomenclature [ 13,141. If there is a choice, it is made on the basis of the greatest number of occurrences of the
`most preferred functional group. Thus aldaric acid > uronic acidketoaldonic acid/aldonic acid > dialdose >
`ketoaldosdaldose > diketose > ketose.
`2.1.2. The parent with the greatest number of carbon atoms in the chain, e.g. a heptose rather than a hexose.
`2.1.3. The parent with the name that comes first in an alphabetical listing based on:
`2.1.3.1. the trivial name or the configurational prefix(es) of the systematic name, e.g. allose rather than
`glucose, a gluco rather than a gulo derivative;
`2.1.3.2. the configurational symbol D rather than L ;
`2.1.3.3. the anomeric symbol a rather than P.
`2.1.4. The parent with the most substituents cited as prefixes (bridging substitution, e.g. 2,3-O-methylene, is
`regarded as multiple substitution for this purpose).
`2.1.5. The parent with the lowest locants (see [14], p. 17) for substituent prefixes.
`2.1.6. The parent with the lowest locant for the first-cited substituent.
`The implications of these recommendations for branched-chain structures are exemplified in 2-Carb- 18.
`Note 1. To maintain homomorphic relationships between classes of sugars, the (potential) aldehyde group of a uronic
`acid is regarded as the principal function for numbering and naming (see 2-Carb-2.2.1 and 2-Carb-22).
`Note 2. To maintain integrity of carbohydrate names, it is sometimes helpful to overstep the strict order of principal
`group preference specified in general organic nomenclature [ 13,141. For example, a carboxymethyl-substituted sugar
`can be named as such, rather than as an acetic acid derivative (see 2-Carb-3 1.2).
`
`0 1996 IUPAC, Pure and Applied Chemistry 68, 1919-2008
`Unauthenticated
`Download Date | 2/29/16 7:57 PM
`
`Luitpold Pharmaceuticals, Inc., Ex. 2024, P.8
`
`Pharmacosmos A/S v. Luitpold Ex. Pharmaceuticals, Inc., IPR2015-01490
`
`

`
`Nomenclature of carbohydrates
`
`1927
`
`2-Carb-2.2. Numbering and naming the parent structure
`The basis for the name is the structure of the parent monosaccharide in the acyclic form. Charts I and IV
`(2-Carb-10) give trivial names for parent aldoses and ketoses with up to six carbon atoms, 2-Carb-8.2 and
`2-Carb- 10.3 describe systematic naming procedures.
`
`FHO
`H-C-OH
`CHpOH
`o-Glyceraldehyde
`O-gIyCerO
`
`FHO
`H-C-OH
`H-C-OH
`CHpOH
`o-Erythrose
`o-erythro
`
`GHO
`HO-C-H
`H-C-OH
`CHpOH
`o-Threose
`0-threo
`
`FHO
`H-C-OH
`H-C-OH
`H-C-OH
`CHpOH
`o-Ribose
`0-rib0
`(o-Rib)
`
`FHO
`HO-C-H
`H-C-OH
`H-C-OH
`CH,OH
`D-Arabinose
`o-arabino
`(o-Ara)
`
`FHO
`H-C-OH
`HO-C-H
`H-C-OH
`CHzOH
`D-xylOSe
`D-XyIO
`(O-xYl)
`
`FHO
`HO-CaH
`HO-C-H
`H-C-OH
`CHpOH
`D-LyXOSe
`
`FHO
`i-C-OH
`i-C-OH
`i-C-OH
`i-C-OH
`CHpOH
`o-Allose
`D-alIO
`(0-All)
`
`FHO
`H O - C + I
`H-C-OH
`H-C-OH
`H-C-OH
`CHpOH
`D-Altrose
`D-altrO
`(D-Alt)
`
`FHO
`H-C-OH
`HO-C-H
`H-C-OH
`H-?-OH
`CHPOH
`o-Glucose
`D-glUC0
`(D-GIG)
`
`GHO
`HO-C-H
`HO-C-H
`H-C-OH
`H-C-OH
`CHpOH
`D-Mannose
`D-mannO
`(D-Man)
`
`FHO
`H-C-OH
`H-C-OH
`HO-C-H
`H-C-OH
`CHzOH
`o-Gulose
`0-gUl0
`(D-Gul)
`
`FHO
`HO-C-H
`H-C-OH
`HO-C-H
`H-C4OH
`CHpOH
`D-ldose
`D-id0
`(D-ldo)
`
`FHO
`H-C-OH
`HO-C-H
`HO-C-H
`H-C-OH
`CHpOH
`D-GalaCtOSe
`0-galacto
`(o-Gal)
`
`FHO
`HO-C-H
`HO-C-H
`HO-C-H
`H-C-OH
`CH,OH
`o-Talose
`O-kllO
`(o-Tal)
`
`Chart I. Trivial names (with recommended three-letter abbreviations in parentheses) and structures (in the
`aldehydic, acyclic form) of the aldoses with three to six carbon atoms. Only the D-forms are shown; the
`L-forms are the mirror images. The chains of chiral atoms delineated in bold face correspond to the
`configurational prefixes given in italics below the names
`
`2.2.1. Numbering
`The carbon atoms of a monosaccharide are numbered consecutively in such a way that:
`2.2.1.1. A (potential) aldehyde group receives the locant 1 (even if a senior function is present, as in uronic
`acids; see 2-Carb-2.1, note 1);
`212.1.2. The most senior of other functional groups expressed in the suffix receives the lowest possible locant,
`i.e. carboxylic acid (derivatives) > (potential) ketonic carbonyl groups.
`2.2.2. Choice of parent name
`The name selected is that which comes first in the alphabet (configurational prefixes included). Trivial names
`are preferred for parent monosaccharides and for those derivatives where all stereocentres are stereochemically
`unmodified.
`
`0 1996 IUPAC, Pure and Applied Chemistry68,1919-2008
`Unauthenticated
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`
`Luitpold Pharmaceuticals, Inc., Ex. 2024, P.9
`
`Pharmacosmos A/S v. Luitpold Ex. Pharmaceuticals, Inc., IPR2015-01490
`
`

`
`1928
`
`Examples:
`
`JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE
`
`CH2OH
`I
`HOCH
`I
`
`c=o
`I
`HOFH
`
`] L-erythro-
`
`CH20H
`I
`HOFH
`HCOH
`I
`H O ~ H
`H ~ H
`I
`HOFH
`HOCH
`I
`CH2OH
`CH20H
`~-elythro-~-gluc0-Non-5-ulose
`L-Glucitol
`not D-gulitol
`not D-threo-D-al/@non-5-uiose
`2.2.3. Choice between alternative names for substituted derivatives
`When the parent structure is symmetrical, preference between alternative names for derivatives should be
`given according to the following criteria, taken in order:
`2.2.3.1. The name including the configurational symbol D rather than L.
`Example:
`
`CHpOH
`I
`HYOH
`HOFH
`HyOMe
`CHzOH
`4-OMethyl-o-xylitol
`not 2-O-methyl-~-xylitol
`2.2.3.2. The name that gives the lowest set of locants (see [ 141, p. 17) to the substituents present.
`Example:
`
`CH20H
`I
`MeOCH
`I
`MeOCH
`HCOH
`I
`HCOMe
`I
`CH20H
`
`2,3,5-Tri-Omethyl-~-mannitol
`not 2,4,5-tri-Omethyl-D-rnannitol
`2.2.3.3. The name that, when the substituents have been placed in alphabetical order, possesses the lowest
`locant for the first-cited substituent.
`Example:
`
`CHpOH
`I
`AcOYH
`HOYH
`HFOH
`HCOMe
`I
`CH20H
`2-OAcetyl-5-O-rnethyl-~-rnannitol
`not 5-Oacety1-2-Omethyl-D-mannitol
`2-Curb-3. The Fischer projection of the acyclic form
`In this representation of a monosaccharide, the carbon chain is written vertically, with the lowest numbered
`carbon atom at the top. To define the stereochemistry, each carbon atom is considered in turn and placed in
`the plane of the paper. Neighbouring carbon atoms are below, and the H and OH groups above the plane of
`the paper (see below).
`
`Unauthenticated
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`Download Date | 2/29/16 7:57 PM
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`Luitpold Pharmaceuticals, Inc., Ex. 2024, P.10
`
`Pharmacosmos A/S v. Luitpold Ex. Pharmaceuticals, Inc., IPR2015-01490
`
`

`
`H e O H
`
`H-C-OH
`
`t
`
`I
`H-c-oH
`I
`
`I
`= H-c-OH
`I
`
`=
`
`(a)
`
`Nornenclafure of carbohydrates
`
`1929
`
`E
`
`H$,H
`
`=
`
`t O H
`
`(9)
`
`I
`HCOH
`I
`(4
`(c)
`(d)
`(b)
`(f)
`Conventional representation of a carbon atom (e.g. C-2 of D-glucose) in the Fischer projection.
`Representation (e) will be used in general in the present document.
`The formula below is the Fischer projection for the acyclic form of D-glucose. The Fischer projections of the
`other aldoses (in the acyclic form) are given in Chart I (2-Carb-2.2).
`
`’CHO
`2 1
`!?OH
`HYYH
`!?OH
`HCOH
`61 CHzOH
`D-Glucose
`Note. The Fischer projection is not intended to be a true representation of conformation.
`2-Carb-4. Configurational symbols and prejkes
`2-Carb-4.1. Use of D and L
`The simplest aldose is glyceraldehyde (occasionally called glyceral [21]). It contains one centre of chirality
`(asymmetric carbon atom) and occurs therefore in two enantiomeric forms, called D-glyceraldehyde and
`L-glyceraldehyde; these are represented by the projection formulae given below. It is known that these
`projections correspond to the absolute configurations. The configurational symbols D and L should appear in
`print in small-capital roman letters (indicated in typescript by double underlining) and are linked by a hyphen
`to the name of the sugar.
`
`CHO
`HO-C-H
`CH20H
`
`CHO
`H-C-OH
`CH~OH
`D-GI yceraldehyde
`2-Carb-4.2. The configurational atom
`A monosaccharide is assigned to the D or the L series according to the configuration at the highest-numbered
`centre of chirality. This asymmetrically substituted carbon atom is called the ‘configurational atom’. Thus if
`the hydroxy group (or the oxygen bridge of the ring form; see 2-Carb-6) projects to the right in the Fischer
`