Pure & Appl.Chem., Vol.54, No.8, pp.1523-1526, 1982.
`Printed in Great Britain.
`
`0033-4545/82/081523-04$03.00/0
`Pergamon Press Ltd.
`
`PROVISIONAL
`
`INTERNATIONAL UNION OF PURE AND APPLIED
`CHEMISTRY
`
`and
`INTERNATIONAL UNION OF BIOCHEMISTRY
`
`JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE*
`
`POLYSACCHARIDE NOMENCLATURE
`
`Comments on these recommendations are welcome and should be sent within 8 months from AuJust 1982 to the
`Secretary of the Commission
`
`Dr. H. B. F. DIXON
`Department of Biochemistry
`University of Cambridge
`Tennis Coun Road
`Cambridge CB2 IQW
`UK
`Comments from the viewpoint of languages other than English are especially encouraged. These may have
`special significance regarding the publication in various countries of translations of the nomenclature eventually
`approved by IUPAC.
`
`•Membership of the Commission for 1979-81 was as follows:
`
`Chairman: P. KARLSON (FRG); Secretary: H. B. F. DIXON (UK); Members: B. L.
`HO RECKER (USA); Y. JEANNIN (France); C. LIEBECQ (Belgium - as Chairman of IUB
`Committee of Editors of Biochemical Journals); B. LINDBERG (Sweden); K. L. LOENING
`(USA); G. P. MOSS (UK); J. REEDIJK (Netherlands); S. F. VELICK (USA); J. F. G.
`VLIEGENTHART (Netherlands).
`Additional contributors to the formulation of these recommendations:
`Nomenclature Committee of IUB (those additional to JCBN): H. BIELKA (GDR); W. B.
`JAKOBY (USA); B. KEIL (France); E. C. WEBB (Australia).
`b.VJ}lfll P41tll.' ll. LINl;lllliR•;; (':"Oll\ltlltr, sw,<11,1n): n , UQIITnN (ll.U); 111111 w ........ ,'1lf.
`(UK); K. L. LOENlNG (USA); D. J. MANNERS (UK); W. G. 6,mflENt> (.'UX); H.
`PAULSEN (FRG); D. A. REES (UK); R. S. TIPSON (USA).
`
`Luitpold Pharmaceuticals, Inc., Ex. 2017, p. 1
`Pharmacosmos A/S v. Luitpold Pharmaceuticals, Inc., IPR2015-01495
`
`

`
`PROVISIONAL
`
`Polysaccharide Nomenclature
`Recommendations 1980•
`IUB-IUPAC JOINT CoMMISSION ON BIOCHEMICAL NOMENCLATURE (JCBN )
`
`The term oligouccharide is commonly used for carbohy(cid:173)
`drates comprised of 2 to about 10 monouccharide reaidu
`.
`2. A polyaaccharid (glycan) compoeed of a aingl
`type of
`monouccharide residue will be named, u a general term, by
`replacing the ending "oee" of the sugar by the suffix "an."
`Note-Exampl a of
`tabliabed uaage of th "an" ending
`are: xylan for polymers of xyloee, mannan for polymers of
`mannoae, and galactan for polyme111 of galactose. Celluloee
`and starch ar both glucana, u they are composed of glucose
`r
`idu
`.
`3. When the configurational series of the monomer residues
`is shown. "o" or " L" may be included in the name of the
`polyaaccharide.
`Examples:
`-4)oGlc(o 1·3)oGlc(o H)oGlc(o 1·3) oGlc(o I·
`
`A o -glucan (nig ran)
`
`S)·O·L-Ara/-0 ..... 5)-cr·L· Araf-(1
`3
`T
`I
`O·L·Araf
`
`5)-cr·L-Araf-(1
`3
`T
`I
`a ·L·Araf
`
`An L-arabinan ' (from muatard eeeda)
`
`5)-o·L·Ar&f·( I
`
`asaigned to newly discoyered polysaccharid a
`4. Nam
`should end in "an."
`Example:
`
`-6)Glc(.81-6)Glc(.81-6)Glc(.81·
`Puatulan (a glucan from the lichen Umbiliroriapuuulala)
`Note-The name ending in "an" refers to the unsubstituted
`polysaccharide. Thus xylan occurs in nature in unacetylated
`ignates unacetylated
`and partially acetylated fon11&. Xylan d
`xylan, and xylan acetate an acetylated xylan.
`5. A polysaccharide (glycan) compoeed entirely of glycu(cid:173)
`ronic sdd reaidu
`is named by replacing "ic acid" by "an."
`Th gen ric nam for this group is "glycuronan."
`Example:
`C02H
`
`-~?1;:,
`co1H
`OH ~Vo;-o,
`OH ~
`OH
`
`A D·galacturonan (pectic acid)
`Note-Th term glycurona.n is used instead .of "polyuron·
`id , " u th latter t rm is incorrect.
`6. A polysaccharide compoeed entirely of amino sugar r
`idues · named by the systematic nomenclature pertinent to
`the amino sugar.
`
`CONTENT
`
`I. Generic lt!.rms
`2. The m aning of -an
`3. Configuration of unita
`4. Naming newly discovered polysaccharides
`5. Uronic acid derivatives
`6. Amino d oxysugar derivatives
`7. Polysaccharid
`composed of more than one kind of reai·
`due
`8. De ignation of link.age
`9. ubstituted r
`idu
`io. Glycoprotein8, proteoglycans, and peptidoglycans
`
`Polysaccharid nom nclature follows the gen ral principles
`of established organic (1) and carbohydrate (2) nomenclature.
`e either Abbreviated Ter(cid:173)
`For abbreviated nomenclature,
`minology of Oligo accharide Chaw, a docum nt being pub(cid:173)
`lished at the same time as this one, for a symbolism that
`explicitly gives all structural features known, or its Appendix
`(altemativ ly Section Lip-3 of Norn nclature of Lipids (3)) for
`a more cond nsed symbolism. Exampl of both symbolisms
`are given herein.
`l. Polysaccharide (glycan) is the name given to a macro(cid:173)
`molecul con isting of a large number of monosaccharide
`joined to each oth r by glyc06idic linkag s.
`(glyco
`) r
`·du
`The term poly(glycose) is not quite a synonym for polysac(cid:173)
`ingle
`trand
`charide (glycan) (cf. Nomenclature of Regular
`Organic Polym 111 (4)), beca
`it includes macromolecules
`composed of glycose residues joined to each other by nongly(cid:173)
`cosidjc linkages.
`Note-Polysaccharides may be lin ar, branched, or cyclic.
`Although most polyaaccharid bear a reducing monosaccha·
`ride residue at one end, and are, therefore, reducing polysac·
`charid
`some polyaaccharid have nonreducing residues at
`both ends.
`containing a substantial proportion of
`For polysaccharid
`amino sugar residues, the term polysaccharide is adequate,
`although the term glycosaminoglycan may be used where
`particular emphas" · d sired.
`Polysaccharides composed of only on kind of monosaccha(cid:173)
`ride are described as homopolysaccharides (homoglycans).
`imilarly, if two or more different kinds of monomeric unit
`are pr
`nt., th cl
`nam of h teropolyaaccharid (hetero·
`glycan) may be used.
`
`• Docum nt ohhe IUB-IUPAC Joint Commiuion on Bioch mical
`o,nenclar.ure (JCBN) whose m mbera are P. Karlaon (Chairman),
`H. B. F. Dixon, Y. Jeannin, C. Li "becq (u Chairman of th
`IUB
`Committee of &litora of Bloch mica! Journala) , B. Lindber,, K. L
`1..oening, G. P. Moes. and S. F. Veliclt. in consultation with J . F. G.
`VII
`ntharl and th Nomenclature Committee of I B , who,,e addl·
`tional m mbera are H. Bielka, W. B. Jakoby, B. Keil, and E. C. W bb.
`Commenu or sugestiona for modifications may be aent to the aec(cid:173)
`retary of JCBN, H. B. F. Dix.on, Department of Bioch miatry, Tennla
`Court Road, Cambridge. United Kin&dom CB2 IQW, or to any
`member. JCBN thanu the expert pan I of B. Lindberg (oonvener),
`D. Horton, the late W. Klyne, K. L. l..oenin,, D. J . Mann ra. W. G.
`Overend, H. Paulaen. D. A. Rees. and R.
`. Tipeon for drafting these
`propoeal&.
`
`I Several of th polyaaccharid
`-ore! reel
`in the exampl have I
`at.ructurea. In lhe structural formulas given for theee, the main augar
`cocnponenu and linupa are pven. but not their proportlooa.
`Reu1ulluLell [1uw iJ.Dwt..C1wm . • Vul . 717, N11 . 7, !'!' ' ""I J- ""14 (•flWJ}
`ey courr@1y or Am@t1Clft !:.6~16ty 6t H1o!og1ca! Chemi~ts, Inc.
`1524
`
`Luitpold Pharmaceuticals, Inc., Ex. 2017, p. 2
`Pharmacosmos A/S v. Luitpold Pharmaceuticals, Inc., IPR2015-01495
`
`

`
`PROVISIONAL: Polyaaccharide nom nclature
`
`1525
`
`Example:
`-4)GlcNAc(Pl-4)GlcNAc(Pl-4)GlcNAc(P(cid:173)
`
`A 2-acetamido-2-deoxy-o-glucan (chitin)
`
`9. When substitution occurs in a polysaocharide (glycsn),
`each substituted type of re idue is made part of the name and
`placed in alphabetical order.
`Examples:
`
`7. A heteropolyaaccharide (heteroglycan) is a polymer con(cid:173)
`taining two or more kinds of sugar (glycuse) or modified sugar
`(for example, aminodeoxyglycose or glycuronlc acid) residue.
`When the polyaaccharid has a principal chain ("backbone")
`composed of only one-type of sugar residue, this sugar residue
`should be written last, with the other ugar residues present
`listed in alphabetical order. However, when no single type of
`sugar re idue constitutes the principal chain, all sugar residues
`should be given alphabetically, and the name terminated with
`the suff"ix glycan.
`Exampl
`:
`
`'~o , o~o, o~o,
`ru~
`HO~
`HO~
`
`OH
`
`LOH OH
`
`'o~Me
`HC>iC
`
`(4-0-Methyl-o -o-glucurono)-o-xylan (from birch, Betula )
`
`•>·Jl-o-Mat1P-(I
`
`•>·P·o-Manp-(1
`6
`
`4l· P·o-Manp-(I - 4l·P·o-Manp-(l-
`6
`
`I
`o-o-Galp
`
`A o-galacto-o-mannan (guarani
`
`o-o-Galp
`
`(A I
`branched o -galacto-o-mannan could be hown in the condensed ayst~m as: [4ManPl·]. 4(Galal -6)ManJll ·
`[<lMan,81-].4(Gala l -6)ManPI-. Note that in the condensed system repeating units are in square brackets and branches in
`parentheses.)
`
`-6)-o-o-Galp-(1 - 6)-a-o-Galp-(1
`2
`f
`
`6)-a -o-Galp-(1 - 6)-a-o-Galp(l-
`2
`
`O·L·Fucp
`
`O·L·Fucp
`3
`T
`I
`o-o-Manp
`
`An L· fuco-o -manno-o-galactan (from a fungus)
`
`-4Man(ll-4Glcfl1 ·4(Gala1 -6)Man,81 -4Man,81 -
`
`A o-galacio-o-gluco·O·mannoglycan (from aofiwood)
`
`8. When th major linkage contained in a homopolysac(cid:173)
`is known, an indication of it may be included in th
`charid
`name. The linkage designation shows the carbon atoms in·
`volved in the glycosidic bonds. When specific ugars are
`d signated. notation for glyco idic linkag
`ahould preced
`the symbols designating the configuration of the ugar; thus,
`(1 ..... 4)-a-o-glucan.
`Examples:
`
`HOH'\~~L,o
`
`HO
`HOH2C
`
`H:2C~:H,O
`
`HO
`
`CH20
`I
`
`HO
`(2 ..... 1)-P-o-Fructofuranan (inulin)
`
`-4)-o-o-Glcp-(l ..... 4)-o-o -Glcp-(l-+ 4)-a-o -Glcp(l-+
`
`(I ..... 4)-a-o-Glucopyranan (amylase)
`
`2,3-Di-0 -ac tyl-6-0 -tritylamylose
`
`10. Polymers r.ontaining covalently bound monosaccharide
`and amino-acid r
`idues are term d glycoproteins, proteogly(cid:173)
`cans, and peptidoglycan .
`Note-It is not possible to give precise distinctions between
`these polymers. In gen ral terms, glycoproteins are conjugated
`proteins containing either oligosaccharide groups or polysac(cid:173)
`charide groups having a fairly low relative molecular maBS.
`Proteoglycans are proteins linked to polysaccharides of high
`molecular mass. Peptidoglycans consist' of polysaccharide
`chains covalently linked to p ptide chains. uch products are
`components of bacterial cell walls.
`
`REFERENCES
`
`I. International Union of Pure and Applied Chem· uy (1979) No (cid:173)
`mrnclalure of Organic Chmtwry, Pergamon, Oxford
`2. Tenlatu1e Ru~" for Carbohydrate Nomeru:lature, t969. Bioclum·
`icaJ Nomrncl<JfU~ and Related Documents, 3rd Ed, 197
`IUB,
`pp. 17•- 195: Bux:hem. J. 125, 673-695 (1 971 ); Biochemu lry 10,
`398:i-4004 and -4995 (1971): Biochim. Bioph)'s. Acla 244, 223-
`
`Luitpold Pharmaceuticals, Inc., Ex. 2017, p. 3
`Pharmacosmos A/S v. Luitpold Pharmaceuticals, Inc., IPR2015-01495
`
`

`
`1526
`
`JOINT COMMISSION ON BIOCliEMICAL NOMENCLATURE
`
`302 (1971); Eur. J. B iachim. 21, 4~77 (1971) ; J. Bi-OL Chem.
`247, 613~ (1972)
`3. The Nomenclature of lipid&. 1976. Bi«hemical Nomf!llclature
`ond Related Documenls, 3rd Ed, 1978, IUB, pp. 122-132; Bi-0·
`
`chem. J . 171, 21-35 (1978); Eur. J. Bi.ochem. 79, 11-21 (1977);
`HopJ)l!·Seyler' Z. PhysioL Chem. 358, 617-631 (1977)
`4. Nomenclature of Regular Single - trOJtd Organic Polymers
`(1976) Pure Appl. Chem. 48, 375-385
`
`Luitpold Pharmaceuticals, Inc., Ex. 2017, p. 4
`Pharmacosmos A/S v. Luitpold Pharmaceuticals, Inc., IPR2015-01495