Third Edition
`
`DATA FOR
`BIOCHEMICAL
`RESEARCH
`
`
`
`Rex M; C. Dawson
`
` Daphne C. Elliott
`William H. Elliott
`Kenneth M. Jones
`
`V
`
`QXFQRB ecannsea mammnang %
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`\DATA for BIOCHEMICAL
`RESEARCH
`
`REXNLC. DAWSON
`
`AFRC Institute of Animal Physiology, Babmham,
`Cambridge
`-
`
`DAPHNE C. ELLIOTT
`
`Flinders University, Bedford Park, South Australia
`
`WILLIAM H. ELLIOTT
`
`University of Adelaide, South Australia
`
`KENNETH M. JONES
`
`University of Leicester
`
`Third Edition
`
`
`
`CLARENDON PRESS ' OXFORD ° 1986
`
`-41
`TEVA PHARMA
`
`I
`
`TEVA EXHIBIT 1013
`USA, INC. V. RB PHARMACEUTICALS LTD.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`' Oxford University Press, Walton Street, Oxford OX2 6D}?
`Oxford New York Toronto
`Delhi Bombay Calcutta Madras Karachi
`Kuala Lumpur Singapore Hong Kong Tokyo
`Nairobi flares Salaam Cape Town
`Melbourne Auckland
`
`and associated companies in
`Beirut Berlin Ibadan Nicosia
`
`Oxford is a trade mark of Oxford University Press
`
`Published in the United States
`by Oxford University Press, New York
`
`© mac. Dawson, o.c. Elliott, w.H. anion, KM Jones, 1986
`
`First edition I 959
`Second edition 1 969
`Third edition 1986
`
`All rights reserved. No part of this publication may be reproduced,
`stored in a retrieval system, or transmitted, in any form or by any means,
`electronic, mechanical, photocopying, recording, or otherwise, without
`the prior permission of Oxford University Press
`
`This book is sold subject to the condition that it shall not, by way
`of trade or otherwise, be lent, re-sold, hired out or otherwise circulated
`without the publisher's prior consent in any form of binding or cover
`other than that in which it is published and without a similar condition
`including this condition being imposed on the subsequent purchaser
`
`British Libraljy Cataloguing in Publication Data
`flare for biochemical research. —3rd ed.
`1. Biological chemistry— Technique
`I. Dawson, R. M. C.
`5 ?4.19'2'028
`QP519. 7
`ISBN 0 -1 9—855358- 7
`
`Library of Congress Cataloging in Publication Eula
`Main entry under title:
`Data for biochemicai research.
`Includes bibliographies and index.
`1. Biological chen:istry—!:'andbooks, manuals, etc.
`I. Dawson, R. M. C. (Rex Malcolm Chaplin}
`QP520. D37 1 985
`5 74.1 9'2'U21
`85-4239
`ISBN 0-—1 9—355358- 7
`
`Set by We Alden Press, London and Northampton
`Printed in Greer Britain by
`R. J. Ac-fora’, Chichesrer, Sussex
`
`'5)‘ '-"
`
`‘
`
`.9
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`Preface
`
`_In this third edition, we again aim to supply information needed by biochemists
`in a form sufficiently concise to be kept in the laboratory. No attempt is made
`to be comprehensive. Material has been selected under the guiding principle that
`it should be of potential use to a reasonably large number of readers. We try, in
`fact,
`to occupy the central ground of possible interest to all biochernists. This
`excludes much material of use only to specialists in individual areas, but they
`will have more comprehensive sources of information in their own fields.
`Between the extremes of obvious material for inclusion, such as buffers, and for
`exclusion, such as rarely encountered metabolites,
`there is a large grey area in
`which subjective decisions have had to be made. Such decisions cannot suit every-
`one or every situation, but we have been encouraged by the sustained interest in,
`and demand for, the previous edition to believe that this policy is supplying a real
`need in the lab oratory.
`Much has been deleted from earlier editions to be replaced by new material
`
`of current importance to biochemistry and molecular biology. With the increase
`in commercial availability of biochemicals, references to preparations have been
`omitted as a routine; with the development of sophisticated separative technolo-
`gies there is less need for references to estimations of many compounds. Refer-
`ences are now included in the general remarks only where they appear to be of use.
`Alphabetical
`listing has been retained but functional groupings of compounds
`has been emphasized so that a reader can see what is available as well as find indi-
`vidual compounds.
`Much of the revision has been done by the authors with help from people
`too numerous to mention individually. Some sections however have been largely
`revised by specialists and these are listed overleaf. It is emphasized that the final
`selection and presentation of material has always beenlmade by the authors who
`must
`therefore bear the responsibility for omissions and deficiencies. Names no
`longer appear at the head of sections because with revisions and reorganizations it
`is difficult to associate any one name with a section. Acknowledgement must be _
`made to contributors to earlier editions on whose work the current volume is
`based.
`
`Babraham, Adelaide, Bedford Park, and Leicester
`July 1984
`
`'W.H.E.
`R.M.C.D.
`D.C.E. K.M.I.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`Acknowledgernents
`
`We gratefully acknowledge the help and assistance of the people listed below in
`the preparation of the sections listed:
`
`9
`
`10
`
`Steroids: Dr R. Searnark, Queen Elizabeth Hospital, University of Adelaide.
`
`Porphyrins and related compounds: Dr J. Barratt, Division of Plant Industry,
`CSIRO, Canberra.
`.
`
`16B Reagents for protein modification; Dr N.M.C. Kaye, Amersharn International
`ple (Cardiff Laboratories), Whitchureh, Cardiff.
`_
`_
`Stability constants for metal complexes: Dr D. Perrin, John Curtin School of
`- Medical Research, Australian National University, Canberra.
`
`17
`
`19
`
`Gel electrophoresis: Dr R. Syrnons, Department of Biochemistry, University
`of Adelaide.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`Contents
`
`Notes on the use of this book
`
`Abbreviations
`1 Amino acids, amines, amides, peptides, and their derivatives
`
`2 Carboxylic acids, alcohols, aldehydes, and ketones
`
`3 Phosphate esters excluding nucleotides and coenzymes
`4 Constituents of nucleic acids and related compounds
`
`A
`
`5 Spectral data and 13K‘, values for purines, pyrimidines, nucleosides, and
`nucleotides
`
`6 Vitamins and co-enzymes
`
`.
`
`7 Carbohydrates and related compounds
`
`'
`
`8 Lipids and long-chain fatty acids
`
`9 Steroids
`
`10 Porphyrins and related compounds
`
`A Bile pigments and related compounds
`
`B Porphyrins (excluding chlorophyll porphyrins)
`
`C Iron porphyrins (haems, haernatins)
`
`D Chlorophylis and related pigments
`
`ll Carotenoids
`12 Plant growth regulators
`
`13 Antimetabolites, antibacterial agents, and enzyme inhibitors
`
`A Compounds affecting nucleic acids
`
`B Protein synthesis inhibitors and amino acid analogues
`
`C Compounds affecting membrane functions
`
`D Inhibitors of mitochondrial and chloroplast function
`
`E Inhibitors of steroid synthesis and function
`
`.
`
`F Other enzyme inhibitors
`
`14 Pharrnacologically active compounds
`15 Artificial and natural substrates
`
`A Electron donors, carriers, and acceptors
`B Substrates for peptidases
`C
`
`C Substrates and inducers for glycosidases
`
`D Substrates for phosphatases
`
`E Substrates for esterases and lipases -
`
`16 Biochemical reagents
`
`A Protective agents
`
`B Reagents for protein modification
`
`”
`
`ix
`
`xi
`1
`
`33
`
`55
`75
`
`1 03
`
`115
`
`141
`
`167
`
`191
`
`213
`
`220
`
`222
`
`228
`
`232
`
`239
`' 245
`
`255
`
`255
`
`275
`
`334
`
`302
`
`312
`
`316
`
`337
`350
`
`350
`360
`
`"364
`
`370
`
`3';'4
`
`379
`
`379
`
`384
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`viii
`
`.
`
`__
`
`_
`
`f
`
`.l
`
`.
`
`—
`
`Contents
`
`S
`
`'_
`
`17 Stability constants for metal complexes
`18 pH, buffers, and physiological media
`_
`19 Gel electrophoresis
`20 Methods for the detection of biochemical compounds on paper and
`thimlayer chromatograms, with some notes on separation
`Ion exchange, gel filtration, and affinity chromatography media
`2]
`22 Isotopic data
`'
`I 23 Biochemical procedures
`24 Definitions, formulae, and general information
`25 Atomic weights
`Index
`
`399
`417
`449
`
`453
`503
`529
`S3’?
`553
`557
`561
`
`—
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`A Notes on the use
`
`this book
`
`I. Tables of bio chemical compounds and comprehensive index of compounds
`
`1. The tables of biochemical compounds are arranged in sections according to
`the type of compound.
`In some instances ambiguity existed as to the correct
`section for a particular compound and here arbitrary decisions have been made.
`Few cross-references between sections or to synonyms have been included, but
`there is a comprehensive index of all compounds‘ and of their commonly used -
`synonyms (p. 561). It
`is strongly advised that this index be used to determine
`whether a compound is included in the tables and to ascertain its location.
`
`2. Melting-points and boiling-points
`
`The value given is that at a pressure of 760 mm of mercury, unless otherwise stated.
`
`3. Optical rotations
`
`The optical activity quoted is the specific rotation, generally for the sodium D
`line, with the temperature of the measurement indicated by a superscript. Where
`other wavelengths have been employed,
`the wavelength is given in A as a sub-
`script. Where given, the concentration of the substance is in g/100 ml.
`
`4. Solubility
`
`Solubilities are given as grams of solute dissolving in 100 ml of solvent. The tem-
`peratures at which solubility data were determined are given as superscripts. Where
`there is no temperature indicated, the data are for room temperature, that is in
`the range 15-25 °C.
`
`I1. References
`
`In general, references are intended to enable readers to find the relevant literature
`on methods and not necessarily to give credit to the main workers in the field.
`References are usually not given to methods of preparation of compounds which
`can be readily obtained commercially at a reasonable price. An abbreviated system
`of references has been used throughout the volume. Authors of individual papers
`have been omitted and for those journals and books which are mentioned most
`frequently the titles have been specially abbreviated as follows:
`
`ABB
`Arm.
`ARB
`BBA
`BBRC
`Ber.
`
`Archives of Biochemistry and Biophysics.
`Licbigfr Annalen der Chemie.
`Annual Review oflliochcmisrry.
`Biochimica et Biophysica Acra.
`Biochemical and Biophysical Research Communications.
`Chcrnische Berickre (prior
`to 1947 Berich re der deutschen
`chemischen Gesellschafi).
`‘
`A
`Biochem. Preps. Biochemical Preparations (Wiley & Sons Inc., New York).
`BJ
`Biochemical Journal.
`'
`BZ
`Biochemiscke Zei tschrift.
`EJB
`European Journal of Biochemistry.
`JA CS
`Journal 0f the American Chemical Society.
`JBC‘
`Jou rnal ofBiological Chemistry.
`
`.
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`xu
`
`'.
`
`"
`
`H
`
`Notes on thense of this book
`
`I
`
`,
`
`Journal of the Chemicai Society.
`JCS
`Journal ofMoIecuIar Biology.
`JMB
`Me th. Biochem. Me zhods of Biochemical Analysis, ed. D. Glick (Wiley-Inter
`Anal.
`science Inc., N.Y.).
`'
`Math. Enzymal. Methods in Enzymology, ed. S.P. Colowick and ND. Kaplan
`(Academic Press).
`Progress in Nucleic Acid Researchand Molecular Biology.
`Proceedings 0f The National Academy of Sciences.
`Proceedings of the Society for Experimen tat Biology and Medi-
`cine.
`Trends in Biochemical Sciences.
`
`PNARMB
`PNAS
`PSEBM
`
`TIBS
`
`ZBC
`
`Hoppe—Seyler'.s' Z eitschrfft filir phystologische Chemie.
`
`For other journals the conventional system of abbreviation has been adopted.
`In certain sections, works of reference which have been quoted extensively in that
`section only have been abbreviated and a note to this effect is included in the
`preamble to the section.
`'
`
`TEVA EXHIBIT 1013
`TE-VA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`Abbreviations
`
`[cu] £3
`
`abs.
`ace[_
`a1k_
`amorph.
`anhyd.
`approx.
`aq.
`benz.
`B_p_
`c
`ca.
`cf.
`ch.
`c.n.s.
`col.
`comp.
`compd.
`cone.
`cryst.
`
`d.
`
`decornp.
`
`deliq.
`deriv_
`diam.
`dil,
`dimorph.
`DMF
`DMSO
`ed.
`efflor.
`equiv.
`esp.
`EST.
`eth.
`evap.
`exptl.
`extr.
`F. p.
`fluor.
`
`A
`F
`g.i.t.
`gl. acetic.
`GLC
`
`‘
`
`de—
`
`specific optical rotation for
`sodium 1)
`line at
`tem-
`perature I
`absolute, absorbance
`acgtgna
`alkajjl-13
`amorphous
`anhydrous
`approximately
`aqueous
`benzene
`b0i]ing_po-mt
`concentration (g/ 100 ml)
`circa = approximately
`compare
`chapter
`central nervous system
`colourless
`competitivefly)
`compound
`concentrated, concentration
`crystals, crystalline, crYstal-
`lization
`with decomposition (after
`M.p. or B.p.), density
`decomposition point,
`composes
`_
`deliquescent
`derivative
`diameter
`, dilute
`dimorphic
`dimethylformamide
`dimethylsulphoxide
`editor, edition
`efflorescent
`equivalent
`especially
`estimation, estimated
`diethyl ether
`evaporates, evaporation
`experimental
`extracted
`freezing-point
`fluorescence
`
`_
`
`"
`
`-
`
`excitation maximum
`fluorescence maximum
`gastro—intestina.1 tract
`glacial acetic acid
`gas-liquid chromatography
`
`gp.
`hex.
`hygr.
`i.
`IDENT.
`i.m.
`il1Ci-
`in01‘g-
`iii5°i-
`i.p.
`i-T-
`lSOL.
`1-"-
`iiq~
`It.
`iiifiifi
`mliiu
`iiii5°-
`monocl.
`M-P-
`i"'-i-“"i-
`110-
`0Pi-
`0fg-
`orthorh_
`P-3 PP.
`path.
`pet. eth_
`ppt.
`pptd.
`pract_
`prep-
`PREP. j
`prism.
`pt.
`PURIF.
`pyr.
`q.v.
`
`recryst.
`rect.
`ref,
`rel.
`resp.
`rh.
`
`group
`hexagonal, hexane
`hygroscopic
`iJ”lS011-lble
`identification
`intramuscular
`ilicilldiflg
`ilmfgaflic
`iiisoiubie
`jfltrapcritofleal
`iiiii3‘i'e¢i
`isolation, isolated
`ifli1"3‘-"$110113
`iiiliiiii
`ilgili
`iiifiii_iiiii-im
`mi-Tilmiim, Hlillliie
`iiiisciiiie
`monoclinic
`mfiiti-|'lg~D0iflt
`m°i'3°i-iiai' Weight
`number
`0Ptim'-ml
`Ofgimic
`orthorhombic
`page, pages
`pathological
`petroleum ether
`precipitate
`precipitated
`practically
`prepared, preparation
`preparation
`prismatic
`point
`purification
`pyridine
`quod vide = which see (in
`cross references}
`recrystallize
`rectangular
`reference
`relativefly)
`respectively
`rhombic
`
`R.T.
`s.
`sat., satd.
`s.c.
`sens.
`
`room _temperature
`soluble
`saturated
`subcutaneous
`sensitivity
`
`‘
`
`_
`
`TEVA EXHIBIT 1013
`_
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`.
`l
`
`'
`
`xii
`s.g.
`
`A
`
`sh
`sl.
`51. 5.
`sol.
`soln-
`soiv,
`sp.
`SP.
`51:. s.
`suppl.
`SYN -
`temp.
`TLC
`to}.
`
`.
`
`'
`specific gravity
`
`'
`
`shoulder
`slight, slightly
`Slightly soluble
`soluble, solubility
`solution
`so1vent(s)
`sparingly, species
`Specific gravity
`sparingly soluble
`supplement
`_
`Synthesis
`temperature
`thin-layer chromatography
`toluene
`
`"
`
`'
`
`tr-
`
`tricl.
`u.v.
`V.
`veg.
`vise.
`vol.
`v.s.
`v. s]. 5.
`v/v
`wh.
`w/v
`w]w
`yei.
`°°
`
`Abbreviations
`
`trace
`
`triclinic
`ultra-violet
`very
`vegetable
`viscous
`volume
`very soluble
`very slightly soluble
`volume for volume
`white
`weight for volume
`weight for weight
`yellow
`completely miscible
`
`-
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`

`
`18 pH,_bi1ffers, and phjrsielpgjcal media
`
`C_'1'tr1'c acid—sod_ium.citrare_' buffer solutions, pH 3.0-6.2
`(N. Hemington and R. M. C. Dawson, unpublished data)
`
`Citric acid monohydrate, C5H3O-, -H20, M. wt. 210.14; 0.1M-solution contains
`21.01 g/l. Trisodium citrate dihydrate, C6 H5 0,Na3 - 2H3 0, M. wt. 294.12; 0.1M-
`solution contains 29.4] g/l.
`_
`x ml 0.1M-citric acid and )2 ml 0.1M-trisodiurn citrate mixed.
`
`pH
`
`30
`33
`34
`33
`33
`4D
`42
`4A
`’ 46
`43
`SD
`52
`SA
`Sfi
`53
`6.0
`62
`
`3: ml 0.1 M-citric acid
`
`y ml 0.1M-trisodium citrate
`
`820
`?7fi
`73B
`6&5
`635
`593
`540
`495
`445
`4&0
`350
`3&5
`255
`2L0
`163
`11.5
`BB
`
`18H
`225
`273
`315
`365
`413
`4&0
`5&5
`555
`503
`653
`695
`745
`793
`843
`88.5
`910
`
`6,11 '-Dimethylglutaric acia'—~NaOH buffer solutions, pH 3 .2-7 .6 at 21 °C
`
`This buffer was outlined by Stafford, Watson, and Ra11d,BBA 18,318 (19S5),for
`use in enzyme studies where low u.v. absorption of the buffer was required. No
`details of mixtures were given. The following approximate pH data were kindly
`supplied by R. Hems.
`fi,{3'-Dirnethylglutaric acid, C71-In O4 , M. wt. 160.2.
`501111 0.1M-5,6’-dimethylglutaric acid (16.02gIl), x ml 0.2M-NaOI-I; diluted to
`100m! with H20.
`
`pH, 21 “C
`32
`34
`35
`33
`43
`42
`4A
`45
`43
`50
`52
`54
`55
`53
`an
`62
`
`GA
`65
`63
`73
`72
`7A
`75
`
`x ml 0.2M-Naou
`415
`735
`113
`133
`16fi5
`184
`193
`2035
`2135
`234
`245
`263
`279
`2935
`325
`3525
`
`3735
`4235
`440
`452
`4605
`46$
`473
`
`‘
`
`428
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.
`
`
`
`TEVA EXHIBIT 1013
`TEVA PHARMACEUTICALS USA, INC. V. RB PHARMACEUTICALS LTD.