Third Edition
`
`DATA FOR
`BIOCHEMICAL E
`RESEARCH
`
`Rex M. C. Dawson
`
`Daphne C. Elliott
`William H. Elliott
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`
`
`Kenneth M. Jones
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`GXFORD SQEEHCE PGBLEQATEQNS
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`DRL — EXHIBIT 1013
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`DRL001
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`DRL - EXHIBIT 1013
`DRL001
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`EEDATA for BIOCHEMICAL
`RESEARCH
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`REX M.C. DAWSON
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`AFRC Institute of Animal Physiology, Babraham,
`Cambridge
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`DAPHNE C. ELLIOTT
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`Flinders University, Bedford Park, South Australia
`
`WILLIAM H. ELLIOTT
`
`University of Adelaide, South Australia
`
`KENNETH M. JONES
`
`University of Leicester
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`
`
`Third Edition
`
`
`
`CLARENDON PRESS ' OXFORD ' 1986
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`‘u’ “‘*M”7r‘1‘*
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`DRL — EXHIBIT 1013
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`DRL002
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`Oxford University Pras, Walton Street, Oxford 0.1’2 6D!’
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`Oxford is a made mark of Oxford Unfvasity Press
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`Published in the United Rates
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`0 .R.M'.C nmaon. D.C. .E'fliott, W.H. Hflott, KM: Jones. I936
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`Hrs: edition 1959
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`Second edition I 969
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`fllird edition 1986
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`All rights reserved. No part ofrhl: publication may be reproduced,
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`stored in a mrieml system, or transmitted, In any form or by any means.
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`electronic. mechanical’. photocopying. recording, or otherwise. without
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`the prforpcnnlnion ofoxfard University has
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`Tmsbookiuoldmbjectto thccondltion thatfldlaflnot, by any
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`of mu}: or otherwire, be lent, re-sold, hind out or otherwise drcuhtad
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`without the pubflahak prior consent In any form ofbinding or cova-
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`oflner than mi: in which it It publtnhed and without a similar condition
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`Including this condition helm impoud on the subsequent purchaser
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`fifth’: Library Catalosltingirt Publication pm
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`and for blodmnloal renmrdz. —3?d ed.
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`1. Notation! clmnlslzv-Technique
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`I. Dawson, R. M C.
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`571.1 9'2'O28
`QP5! 9. 7
`ISBN 0-I 9-—855358- 7
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`Library of Congress Chtafoging in Publication am
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`Main entry under title.‘
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`Data for blochenlioal research.
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`Indudes bibliogmpvhia and index.
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`I. Bloiogicul chenlfstly-Handbooks, nunuals, etc.
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`I. Dawson. R. M. C‘. (Rex Malcolm Chaplin)
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`99520.03? 1985
`574.1 9'2'02I
`85-4239
`ISBN 0-1 9—855358- 7
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`Set by The Alden Press, London and Northampton
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`hinted in Grant fldtain by
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`R. J. Acfard, Olidtexter, Sussex
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`DRL - EXHIBIT 1013
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`DRL - EXHIBIT 1013
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`Preface
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`in this third edition, we again aim to supply information needed by biochemists
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`in a fonn sufficiently concise to be kept in the laboratory. No attempt is made
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`to be comprehensive. Material has been selected under the guiding principle that
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`it should be of potential use to a reasonably large number of readers. We try, in
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`fact,
`to occupy the central ground of possible interest to all biochernists. This
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`excludes much material of use only to specialists in individual arms, but they
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`will have more comprehensive sources of information in their own fields.
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`Between the extremes of obvious material for inclusion, such as buffers, and for
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`exclusion, such as rarely encountered metabolites, there is a large grey area in
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`which subjective decisions have had to be made. Such decisions cannot suit every-
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`one or every situation, but we have been encouraged by the sustained interest in,
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`and demand for, the previous edition to believe that this policy is supplying a real
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`need in the laboratory.
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`Much has been deleted from earlier editions to be replaced by new material
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`of current importance to biochemistry and molecular biology. With the increase
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`in commercial availability of biochernlcals, references to preparations have been
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`omitted as a routine; with the development of sophisticated separative technolo-
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`gies there is less need for references to estimations of many compounds. Refer-
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`ences are now included in the general remarks only where they appear to be of use.
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`Alphabetical
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`has been emphasized so that a reader can see what is available as well as find indi-
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`vidual compounds.
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`Much of the revision has been done by the authors with help from people
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`too numerous to mention individually. Some sections however have been largely
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`revised by specialists and these are listed overleaf. It is emphasized that the final
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`selection and presentation of material has always been made by the authors who
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`must therefore bear the responsibility for omissions and deficiencies. Names no
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`longer appear at the head of sections because with revisions and reorganizations it
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`is difficult to associate any one name with a section. Acknowledgement must he _
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`made to contributors to earlier editions on whose work the current volume is
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`based.
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`Babnrhcm, Adelaide, Betlfard Hark, and Leicester
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`July I 934
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`R.M.C.D. 'W.I-LE.
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`D.C.E. K.MJ.
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`DRL - EXHIBIT 1013
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`DRL004
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`DRL - EXHIBIT 1013
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`Acknowledgements
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`We gratefully acknowledge the help and assistance of the people listed below in
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`the preparation of the sections listed:
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`16B
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`Steroids: Dr R. Seamark, Queen Blimbeth Hospital, University of Adelaide.
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`Porphyrins and related compounds: Dr J. Barrett, Division of Plant Industry,
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`CSIRO, Canberra.
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`Reagents for protein modification: Dr N.M.C. Kaye, Amersham International
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`plc (Cardiff Laboratories), Whitchurch, Cardiff.
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`Stability constants for metal complexes: Dr D. Penin, John Curtin School of
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`Medical Research, Australian National University, Canberra.
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`Gel electrophoresis: Dr R. Symons, Department of Biochemistry, University
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`of Adelaide.
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`Contents
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`Notes on the use of this book
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`Abbreviations
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`1 Amino acids, amines, amides, peptides, and their derivatives
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`2 Carboxylic acids, alcohols, aidehydes, and iretones
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`3 Phosphate esters excluding nucleotides and coenzymes
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`4 Constituents of nucleic acids and related compounds
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`5 Spectral data and pK, values for purines, pyrimidines, nucleosides, and
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`nucleotides
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`6 Vitamins and coenzyrnes
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`7 Carbohydrates and related compounds
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`8 Lipids and long-chain fatty acids
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`9 Steroids
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`10 Porphyrins and related compounds
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`A Bile pigments and related compounds
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`B Porphyrins (excluding chlorophyll polphyrinsl
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`C Iron porphyrins (baerns. haematins)
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`D Chiorophyils and related pigments
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`ll Carotenoids
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`12 Plant growth regulators
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`13 Antimetaboiites, antibacterial agents, and enzyme inhibitors
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`A Compounds affecting nucleic acids
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`B Protein synthesis inhibitors and amino acid analogues
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`C Compounds affecting membrane functions
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`D inhibitors of mitochondrial and chloroplast fimctlon
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`E Inhibitors of steroid synthesis and function
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`F Other enzyme inhibitors
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`14 Pharmacologicaliy active compounds
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`I5 Artificial and natural substrates
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`A Electron donors. carriers, and acceptors
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`B Substrates for peptidases
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`C Substrates and inducers for glyeosidascs
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`D Substrates for phospbatases
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`E Substrates for esterases and lipans -
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`16 Biochemical reagents
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`A Protective agents
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`3 Reagents for protein modification
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`1
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`ix
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`xi
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`33
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`ss
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`141
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`103
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`191
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`33?
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`viii
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`Contezm
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`17 Stability constants for metal complexes
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`18 pH, buffers, and physiological media
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`19 Gel electrophoresis
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`20 Methods for the detection of biochemical compounds on paper and
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`thin-layer chromatogmms, with some notes on separation
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`[on exchange, gel filtration, and affinity chromatography media
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`22 Isotopic data
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`23 Biochemical procedures
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`24 Definitions, formulae, and general information
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`25 Atomic weights
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`399
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`417
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`449
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`529
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`553
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`557
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`53?
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`Index
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`DRL - EXHIBIT 1013
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`C Notes on the use of this book
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`1. Tables of biochemical compounds and compreheve index of compounds
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`I. The tables of biochemical compounds are arranged in sections according to
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`the type of compound. In some instances ambiguity existed as to the correct
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`section for a particular compound and here arbitrary decisions have been made.
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`Few cross-references between sections or to synonyms have been included, but
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`there is a comprehensive index of all compounds and of their commonly used -
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`synonyms (p. 561). It is strongly advised that this index be used to determine
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`whether a compound is included in the tables and to ascertain its location.
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`2. Melting-points and boiling-pain ts
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`The value given is that at a pressure of 760 mm of mercury, unless otherwise stated.
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`3. Optical rotation:
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`The optical activity quoted is the specific rotation, generally for the sodium D
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`line, with the temperature of the measurement indicated by a superscript. Where
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`other wavelengths have been employed, the wavelength is given in A as a sub-
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`script. Where given, the concentration of the substance is in g] 100 ml.
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`4. Solubility
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`Solubilities are given as grams of solute dissolving in 100 ml of solvent. The tem-
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`peratures at which solubility data were determined are given as superscripts. Where
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`there is no temperature indicated, the data are for room temperature, that is in
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`the range 15-25 °c.
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`II. References
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`In general, references are intended to enable readers to find the relevant literature
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`on methods and not necessarily to give credit to the main workers in the field.
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`References are usually not given to methods of preparation of compounds which
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`can be readily obtained commercially at a reasonable price. An abbreviated system
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`of references has been used throughout the volume. Authors of individual papers
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`have been omitted and for those journals and books which are mentioned most
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`frequently the titles have been specially abbreviated as follows:
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`Archives of Biochemistry and Biophysics.
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`Lie big’; Annalen o'er Chemie.
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`Annual Reiyiew of Biochemistry.
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`Biochimica er Biophysica Acta.
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`Biochemical and Biophysical Research Communications.
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`Chemische Berichte (prior
`to 1947 -Berich re der deurschen
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`chemischen Gesellschaft).
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`Biochem. Preps. Biochemical Preparations (Wiley & Sons Inc., New York).
`BI
`Biochemical Journal.
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`.32
`Biochcmische Zeirsclmfi‘.
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`European Journal of Biochemistry.
`1333
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`Journal of the American Chemical Society.
`JACS
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`Journal 01' Biological Chemistry.
`JBC
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`.
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`DRL - EXHIBIT 1013
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`DRL008
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`ABE
`Ann.
`ARE
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`BBA
`BBRC
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`Ber.
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`DRL - EXHIBIT 1013
`DRL008
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`x
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`Notesontheuseofthishoolc
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`Journal of the Chemical Society.
`JCS
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`Journal offloleculer Biology.
`JMB
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`Merh. Blocllem. Methods of Biochemical Analysis, ed. D. Glick (\Viley-Inter-
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`Anal.
`science 1110., N.Y.).
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`Math. Enzymol. Methods in Enzymology, ed. S.P. Colowiek and 14.0. Kaplan
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`(Academic Press).
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`Progress in Nucleic Acid Research "and Molecular Biology.
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`Proceedings of The National Academy of Sciences.
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`Proceedings of the Society for Experimental Biology and Medi-
`cine.
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`.'D'end.t in Biochemical Sciences.
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`Hoppe-Seylertr Zeirschrlft fiir plrysfologlsche Claemie.
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`PNARMB
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`PNAS
`PSEBH
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`TIES
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`ZPC
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`For other journals the conventional system of abbreviation has been adopted.
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`In certain sections, works of reference which have been quoted extensively in that
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`section only have been abbreviated and a note to this effect is included in the
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`preamble to the section.
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`DRL — EXHIBIT 1013
`
`DRL009
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`DRL - EXHIBIT 1013
`DRL009
`
`

`
`Abbreviations
`
`
`
`
`870“?
`
`
`hexagonal, hexane
`
`hygroscopic
`insoluble
`
`identification
`
`intramuscular
`
`including
`inorganic
`insoluble
`
`intraperitoneal
`infra-red
`
`
`
`isolation, isolated
`intravenous
`
`
`liquid
`
`light
`maximum
`
`
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`
`
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`
`
`
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`
`
`
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`hex.
`
`hvsr.
`
`IDENT.
`
`i.m.
`
`
`
`inorg.
`insol.
`
`
`i.p.
`i.r.
`
`I301...
`
`
`
`
`
`
`
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`
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`
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`
`
`M.wt.
`
`
`
`
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`
`
`
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`
`
`
`
`
`
`
`specific optical rotation for
`sodium D line at
`tem-
`
`
`
`
`
`perature t
`absolute, absorbanoe
`acetone
`alkaline
`
`
`
`
`
`
`
`amorphous
`
`anhydrous
`approximately
`aqueous
`benzene
`
`
`
`
`
`
`
`
`
`
`la] is
`
`abs.
`
`acct.
`
`elk.
`
`arnorph.
`
`anhyd.
`approx.
`
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`
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`deriv.
`
`minimum, minute
`miscible
`
`monoclinic
`
`
`melting-point
`
`molecular weight
`number
`
`
`optimum
`
`organic
`orthorhombic
`
`
`pase. vases
`
`pathological
`
`
`petroleum ether
`
`precipitate
`precipitated
`
`practically
`
`prepared, preparation
`
`preparation
`
`prismatic
`
`point
`purification
`
`pyridine
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`
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`quod vide = which see (in
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`relativefly)
`
`respectively
`rhombic
`
`
`room temperature
`soluble
`
`saturated
`
`subcutaneous
`
`
`sensitivity
`
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`DRL - EXHIBIT 1013
`
`'
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`DRL010
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`boiling-point
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`concentration (31100 mi)
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`circa = approximately
`
`compare
`
`chapter
`
`
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`central nervous system
`colourless
`
`competitivefly)
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`compound
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`concentrated, concentration
`
`
`crystals, crystalline, crystal-
`lization
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`with decomposition (after
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`
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`11.13. or 13.13.), density
`
`
`decomposition point, de-
`composes
`cleliquescent
`derivative
`
`diameter
`
`dilute
`
`
`dimorphic
`dimethylformamide
`dimethylsulphoxide
`
`
`editor, edition
`efflorescent
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`dirnorph.
`
`DMP
`
`DMSO
`
`grimy.
`equiv.
`ESP-
`asr.
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`evap.
`exptl.
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`equivalent
`
`especially
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`estimation, estimated
`
`
`diethyl ether
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`evaporates, evaporation
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`experimental
`extracted
`
`freezing-point
`fluorescence
`
`excitation maximum
`
`
`fluorescence maximum
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`
`
`gastrointestinal tract
`
`
`
`glacial acetic acid
`_
`
`gas-liquid chromatography
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`DRL - EXHIBIT 1013
`DRL010
`
`

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`specific gravity
`shoulder
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`slight. slightly
`
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`slightly soluble
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`soluble, solubility
`solution
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`sparingly soluble
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`supplement
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`synthesis
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`temperature
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`thin-layer chromatography
`toluene
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`vléu.
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`Abbreviations
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`trace
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`trlclinic
`
`ultra-violet
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`V011?
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`vegetable
`viscous
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`volume
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`
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`very soluble
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`very slightly soluble
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`volume for volume
`white
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`
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`weight for volume
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`weight for weight
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`yellow
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`completely miscible
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`-
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`DRL - EXHIBIT 1013
`
`DRL01 1
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`DRL - EXHIBIT 1013
`DRL011
`
`

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`13 pa. buffers, and physiological media
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`(.'Ytrz'c acr'd-sodium citrate‘ buffer solutions, pH 3.0-6.2
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`(N. I-Iemington and R. M. C. Dawson, unpublished data)
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`Citric acid monohydrate, C5 Hg 0-, -H, 0, M. wt. 210.14; 0.1M-solution contains
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`21.01 gll. Trisodium citrate dihydrate, C5H50-;Na3 -2H, 0, M. wt. 294.12; 0.1M-
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`solution contains 29.41 gll.
`_
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`x ml 0.1M-citric acid and y ml 0.1 M-trisodium citrate mixed.
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`y mi 0.1M-afsodium citrate
`18.0
`22.5
`21.0
`31.5
`36.5
`41.0
`46.0
`50.5
`55.5
`60.0
`65.0
`69.5
`74.5
`79.0
`84.0
`88.5
`92.0
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`
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`x ml 0.1M-citric acid
`82.0
`
`77.5
`
`?3.0
`68.5
`63.5
`59.0
`54.0
`49.5
`44.5
`40.0
`35.0
`30.5
`25.5
`21.0
`16.0
`11.5
`8.0
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`pH
`3.0
`3.2
`3.4
`3.6
`3.8
`4.0
`4.2
`4.4
`' 4.6
`4.8
`5.0
`5.2
`5.4
`
`5.6
`5.8
`6.0
`6.2
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`B,fl'-Dimethylgluraric r:ci:2'—Na0H buffer sohmions, pH 3 .2-7 .6 at 21 °C
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`This buffer was outlined by Stafford, Watson, and R.and,BBA 18, 318 (1955), for
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`use in enzyme studies where low u.v. absorption of the buffer was required. No
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`details of mixtures were given. The following approximate pH data were kindly
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`supplied by R. Heme.
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`13,13’-Dixnethylglutafic acid , C-,1-In 04 , M. wt. 160.2.
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`50ml 0.1M-5,13’-dirnethylglutaric acid (l6.02gIl), x ml 0.2M-Na0H; diluted to
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`100111] with H10.
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`.1; ml 0.215-NaOH
`4.15
`7.35
`1 1 .0
`13.7
`16.55
`13.4
`19.9
`20.85
`21.95
`23.1
`245
`26.0
`27.9
`29.35
`32.5
`
`35.25
`37.75
`42.35
`44.0
`45.2
`46.05
`
`45.6
`47.0
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`'
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`pH, 21 ‘C
`3.2
`3.4
`3 .5
`3.8
`4.0
`4.2
`4.4
`4.6
`4.3
`5.0
`5.2
`5.4
`5.6
`5.3
`6.0
`6.2
`6.4
`6.5
`5.3
`7.0
`7.2
`7.4
`7.6
`
`
`
`428
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`DRL - EXHIBIT 1013
`
`DRL012
`
`DRL - EXHIBIT 1013
`DRL012