HANDBOOK
`Mi
`CHEMISTRY
`aM
`debe(Ge
`
`
`CRC PRESS
`
`EDITION
`2003-2004
`
`DAVID R. LIDE
`Editor-in-Chief
`
`WW
`
`
`
`MYLAN INST. EXHIBIT 1102 PAGE 1
`
`MYLAN INST. EXHIBIT 1102 PAGE 1
`
`

`

`CRC Handbook
`of
`Chemistry and Physics
`
`A Ready-Reference Book of Chemical and Physical Data
`
`
`
`Editor-in-Chief
`
`David R. Lide, Ph.D.
`Former Director, Standard Reference Data
`National Institute of Standards and Technology
`
`CRC Press
`Boca Raton London New York Washington, D.C.
`
`MYLANINST. EXHIBIT 1102 PAGE 2
`
`MYLAN INST. EXHIBIT 1102 PAGE 2
`
`MYLAN INST. EXHIBIT 1102 PAGE 2
`
`

`

`© 1974, 1975, 1976, 1977, 1978, 1979, 1980, 1981, 1982, 1983, 1984, 1985, 1986, 1987, 1988, 1989, 1990, 1991, 1992, 1993, 1994, 1995, 1996,
`1997, 1998, 1999, 2000, 2001, 2002, 2003 by CRC Press LLC
`
`© 1964, 1965, 1966, 1967, 1968, 1969, 1970, 1971, 1972, 1973 by THE CHEMICAL RUBBER CO.
`Copyright 1918, 1920 by The Chemical Rubber Company (Copyright renewed 1946, 1948 by The Chemical Rubber Publishing Company)
`
`Copyright 1922 (Copyright renewed 1950), 1925 (Copyright renewed 1953), 1926 (Copyright renewed 1954), 1927 (Copyright renewed 1955),
`1929 (Copyright renewed 1957), 1936, 1937 (Copyright renewed 1965 by The Chemical Rubber Co.), 1939, 1940 (Copyright renewed 1968 by
`the Chemical Rubber Co.), 1941 (Copyright renewed 1969 by The Chemical Rubber Co. ), 1942 (Copyright renewed 1970 by The Chemical Rubber
`Co,), 1943 (Copyright renewed 1971 by The Chemical Robber Co,), 1944 (Copyright renewed 1972 by The Chemical Rubber Co.), 1945 (Copyright
`renewed 1973 by The Chemical Rubber Co,), 1947, 1949, 1950, 1951, 1952 (Copyright tenewed 1980 by CRC Press, Inc.), 1953 (Copyright
`renewed 1981aby CRC Press,Inc.), 1954 (Copyright renewed 1982 by CRC Press, Inc.), 1955(Copyright renewed 1983 by CRC Press, Inc.), 1956
`by Chemical Rubber Publishing Company
`
`® 1957, 1958, 1959, 1960, 1962 by Chemical Rubber Publishing Company
`«
`
`This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources
`are indicated, A wide variety of references are listed, Reasonable efforts have been made to publish reliable data and information, but the author
`and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use.
`
`Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying,
`microfilming, and recording, or by any information storage or retrieval system, without prior permission in writing from the publisher.
`
`All rights reserved. Authorization to photocopy. itemsfor internal or personal use, or the personal or internal use of specific clients, may be granted
`by CRC Press LLC, provided that $1.50 per page photocopied is paid directly to Copyright Clearance Center, 222 Rosewood Drive, Danvers, MA
`01923 USA. The fee code for users of the Transactional Reporting Service is ISBN 0-8493-0484-9/03/$0,00+$ 1,50. The fee is subject to change
`without notice. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged.
`
`CRC Press LLC's consent does not extend to copying for general distribution, for promotion, for creating new works, or for resale. Specific
`permission must be obtained in writing from CRC Press for such copying.
`
`Direct all inquiries to CRC Press LLC, 2000 N.W., Corporate Blvd., Boca Raton, Florida 33431.
`
`Visit the CRC Press Web site at www.crcpress.com
`
`© 2003 by CRC Press LLC
`No claim to original U.S. Government works
`International Standard Book Number 0-8493-0484-9
`Library of Congress Card Number 13-11056
`Printed in the United States of America | 234567890
`Printed on acid-free paper
`
`MYLANINST. EXHIBIT 1102 PAGE 3
`
`MYLAN INST. EXHIBIT 1102 PAGE 3
`
`MYLAN INST. EXHIBIT 1102 PAGE 3
`
`

`

`This table gives selected properties of some important amino acids and closely related compounds. The first part ofthe table lists the 20 “standard”
`amino acids that are the basic constituents of proteins (structures of these amino acids may be found in the following table). The second part includes
`other amino acids and related compounds of biochemical importance. Within each part of the table the compounds are listed by name in alphabetical
`order.
`
`Symbol — Three-letter symbol for the standard amino acids
`M, — Molecular weight
`tm — Melting point
`pX, . pX;,, pK. . pXg — Negative of the logarithm of the acid dissociation constants for the COOH and NH; groups
`(and, in some cases, other groups) in the molecule (at 25°C)
`pl — pHatthe isoelectric point
`S — Solubility in water at 25°C in units of grams of compound per kilogram of water; when quantitative data are not
`available, the notationssl.s. (for slightly soluble) and v.s. (for very soluble) are used.
`
`Data on the enthalpy of formation of many of these compounds are included in the table “Standard Thermodynamic Properties of Chemical
`Substances”in Section 5 of this Handbook. Absorption spectra and optical rotation data can be found in Reference 3, Partial molar volume and other
`thermodynamic properties, including solubility as a function of temperature, are given in References 3 and 5. Most of the pK values come from
`Reference 7.
`
`REFERENCES
`
`SeeSee
`
`8.
`
`Dawson, R. M. C., Elliott, D, C., Elliott, W. H., and Jones, K. M., Datafor Biochemical Research, 3rd ed., Clarendon Press, Oxford, 1986.
`Budavari, S., Ed., The Merck Index, Twelfth Edition, Merck & Co., Rahway, NJ, 1996.
`Sober, H. A., Ed., CRC Handbook ofBiochemistry. Selected Datafor Molecular Biology, CRC Press, Boca Raton, FL, 1968.
`Voet, D. and Voet, J. G., Biochemistry, Second Edition, John Wiley & Sons, New York, 1995.
`Hinz, H. J., Ed., Thermodynamic Data for Biochemistry and Biotechnology, Springer-Verlag, Heidelberg, 1986.
`Fasman, G. D,, Ed., Practical Handbook of Biochemistry and Molecular Biology, CRC Press, Boca Raton, FL, 1989.
`Smith, R. M., and Martell, A. E., NIST Standard Reference Database 46: Critically Selected Stability Constants of Metal Complexes
`Database, Version 3.0, National Institute of Standards and Technology, Gaithersburg, MD, 1997.
`Jin, Z. and Chao, K. C., J. Chem. Eng. Data, 37, 199, 1992.
`
`The standard amino acids:
`
`Symbol
`
`Name
`
`Mol. form.
`
`M,
`
`tefC
`
`pk,
`
`pX,
`
`pk,
`
`pl
`
`S/g kg"
`
`12.10
`
`3.71
`8.14
`4.15
`
`6.04
`
`
`
`165.0
`6.00
`9.71
`2,33
`297
`89.09
`CH,NO,
`Alanine
`Ala
`182.6
`10.76
`9.00
`2.03
`244
`«174.20
`CsH,yNjO,
`Arginine
`Arg
`25.1
`5.41
`8.73
`2.16
`235
`132.12
`CyH,N,0,
`Asparagine
`Asn
`4.95
`2.77
`9.66
`1.95
`270
`133.10
`CyHjNO,
`Aspartic acid
`Asp
`v.8.
`5.07
`10.28
`1.91
`240
`121.16
`C,H;NO,S
`Cysteine
`Cys
`8.61
`3.22
`9.58
`2.16
`160
`147.13
`CsHjNO,
`Glutamic acid
`Glu
`42
`5.65
`9.00
`2.18
`185
`146,15
`CsHjoN20,
`Glutamine
`Gin
`250.9
`5.97
`9.58
`2.34
`290
`75,07
`C,H,NO,
`Glycine
`Gly
`43.5
`7.59
`9.09
`1.70
`287
`155.16
`C.H5N,O,
`Histidine
`His
`34.2
`6.02
`9.60
`2.26
`284
`131.17
`CsH,,NO;
`Isoleucine
`Ile
`22.0
`5.98
`9.58
`2.32
`293
`131.17
`CsH,,NO;
`Leucine
`Leu
`
`
`
`
`Lys 146.19=224Lysine CyH,4N.0, 2.15 9.16 10,67 9.74 5.8
`
`
`
`Met
`Methionine
`CsH,,NO,S
`—:149.21
`281
`2.16
`9.08
`5.74
`56
`
`
`
`
`Phe 165.19=283Phenylalanine CgH,,NO, 2.18 9.09 5.48 27.9
`
`
`
`Pro
`Proline
`CsHNO,
`115.13
`221
`1.95
`10.47
`6.30
`1623
`Ser
`Serine
`C,H;NO,
`105.09
`228
`2.13
`9.05
`5.68
`50.2
`Thr
`Threonine
`CyH.NO,
`119.12
`256
`2.20
`8.96
`5.60
`98.1
`Trp
`Tryptophan
`CyHyN,0O,
`204.23
`289
`2,38
`9.34
`5.89
`13.2
`
`
`
`
`Tyr 181.19=343Tyrosine CyH,,NO, 2.24 9.04 10.10 5.66 0.46
`
`
`
`Val
`Valine
`C;H,,NO,
`117.15
`315
`2.27
`9.52
`5.96
`88.5
`
`
`
`7-1
`
`MYLANINST. EXHIBIT 1102 PAGE 4
`
`MYLAN INST. EXHIBIT 1102 PAGE 4
`
`MYLAN INST. EXHIBIT 1102 PAGE 4
`
`

`

`Other amino acids and related compounds:
`
`Name
`
`N-Acetylglutamic acid
`N6-Acetyl-L-lysine
`B-Alanine
`DL-2-Aminobutanoic acid
`DL-3-Aminobutanoic acid
`4-Aminobutanoic acid
`5-Aminolevulinic acid
`L-3-Amino-2-
`
`methylpropanoic acid
`Azaserine
`L-y-Carboxyglutamic acid
`Carnosine
`Citrulline
`Creatine
`L-Cysteic acid
`L-Cystine
`L-3,5-Diiodotyrosine
`Dopamine
`L-Ethionine
`Glycocyamine
`N-Glycylglycine
`Histamine
`
`Homocysteine
`Homocystine
`L-Homoserine
`
`5-Hydroxylysine
`trans-4-Hydroxyproline
`L-3-lodotyrosine
`L-Kynurenine
`L-Lanthionine
`Levodopa
`2-Methylalanine
`L-|-Methylhistidine
`L-Norleucine
`L-Norvaline
`L-Ornithine
`
`O-Phosphoserine
`L-Pyroglutamic acid
`Sarcosine
`
`L-Thyroxine
`
`Mol. form.
`
`C;H,,NO,
`CgHi6N205
`C,H,NO;
`CyHyNO,
`C4HyNO,
`C,H,NO,
`CsHNO;
`CyHgNO,
`
`CsH7N30q
`CoHyNOg
`CgH,4N,O5
`CeH) N30,
`C,HN,O,
`C,H,NO,S
`CsH2N,0,5;
`CoHol,NO,
`CyH| NO,
`CgH)3NO,S
`C;H,N,0,
`C4HgN20,
`CsHoNy
`C,HjNO,S
`CgH6N20,8.
`CyHyNOs
`CoH\4N20,
`CsH,NO,
`CoH olNO,
`CioHj.N20,
`CeH)2N,0,8
`CyH, NO,
`CyHgNO
`CyH);N,O0,
`CoH NO;
`CsH, NO,
`CsH)2N;,02
`C;H,NO,P
`C.H;NO,
`C,H,NO,
`CysH)14NO,
`
`189.17
`188.23
`89.09
`103.12
`103.12
`103.12
`131.13
`103,12
`
`173.13
`191.14
`226.24
`175.19
`131.13
`169.16
`240.30
`432.98
`153.18
`163.24
`7.11
`132.12,
`111.15
`135.19
`268.36
`119.12
`162.19
`131.13
`307.09
`208.22
`208.24
`197.19
`103.12
`169.18
`131.17
`117.15
`132.16
`185.07
`129.12
`89.09
`716.87
`
`pA,
`
`pK.
`
`pk,
`
`Sigkg'
`
`199
`265
`200
`
`194
`203
`118
`183
`
`150.
`167
`
`213
`
`273
`282
`263
`83
`232
`264
`203
`
`274
`205
`185
`
`277
`335
`
`30)
`
`140
`166
`162
`212
`235
`
`2.12
`3.51
`2.30
`3.43
`4.02
`4.05
`
`1.70
`2.51
`2.32
`2.63
`1.89
`1.50
`2.12
`
`2.18
`2.82
`3.13
`
`2.15
`1.59
`2.27
`2.13
`1.82
`2.20
`
`2.20
`2.36
`
`2.31
`2.31
`1.94
`2.14
`3.32
`2.18
`2.20
`
`9.51
`10.08
`9.63
`10.05
`10.35
`8.90
`
`8.55
`9.90
`9.35
`9.30
`14.30
`8.70
`8.80
`9.10
`10.36
`9.05
`
`8.10
`9.83
`8,57
`9.44
`9.28
`8.85
`9.47
`9.10
`
`8.75
`10.21
`8.85
`9.68
`9.65
`8.78
`9.80
`
`9.97
`10.01
`
`891
`210
`1250
`v.8.
`
`vs.
`
`322
`
`v.8.
`0.11
`0,62
`
`v.58.
`
`0.2
`1100
`
`361
`sls.
`sls.
`1.5
`1650
`137
`
`15
`107
`v.58.
`
`428
`sls.
`
`3.20
`
`8.03
`
`8.52
`
`4.75
`6.76
`
`1.30
`2.05
`6.16
`8.88
`13.10
`
`6.11
`10.38
`2.54
`
`9.83
`
`8.70
`
`9.81
`
`13.40
`
`6.48
`
`10.52
`5.70
`
`6.45
`
`7-2
`
`MYLANINST. EXHIBIT 1102 PAGE 5
`
`MYLAN INST. EXHIBIT 1102 PAGE 5
`
`MYLAN INST. EXHIBIT 1102 PAGE 5
`
`