Amino Acid Analysis Protocols (Methods in Molecular Biology Vol 159)

278 Pages·2001·1.36 MB·English

by  Cooper C.

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Amino Acid Analysis Protocols
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M E T H O D S I N M O L E C U L A R B I O L O G YTM
Amino Acid Analysis
Protocols
Edited by
Catherine Cooper
Nicolle Packer
and
Keith Williams
Proteome Systems Ltd, North Ryde, Australia
Humana Press Totowa, New Jersey
© 2001 Humana Press Inc.
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Library of Congress Cataloging-in-Publication Data
Amino acid analysis protocols / edited by Catherine Cooper, Nicolle Packer and Keith Williams.
p. cm. -- (Methods in molecular biology ; 159)
Includes bibliographical references and index.
ISBN 0-89603-656-1
1. Amino acids--Analysis. I. Cooper, Catherine, 1970- II. Packer, Nicolle. III.
Williams, Keith, 1948- IV. Methods in molecular biology (Clifton, N.J.) ; v. 159.
QD431.25.A53 A45 2000
547'.75046--dc21
00-023798
Preface
Amino acid analysis is a technique that has become commonplace in
biotechnology, biomedical, and food analysis laboratories. This book describes
a variety of amino acid analysis techniques and how each technique can be
used to answer specific biological questions.
The first two chapters in Amino Acid Analysis Protocols introduce the
concepts, basic theory, and practice of amino acid analysis. The following
chapters give detailed instructions on various methods and their applications.
As highlighted, there are many different approaches to amino acid analy-
sis, but in all cases the results depend heavily on the quality of the sample.
Therefore a new way to desalt samples prior to hydrolysis is covered as an
introductory chapter (Chapter 3), and most authors have devoted a section to
sample preparation, especially to the collection and storage of bodily fluids.
Some of the amino acid analysis methods described in this book are based
on HPLC separation and analysis after precolumn derivatization. Theprecolumn
derivatization techniques described use (a) 6-aminoquinolyl-N-hydroxy-
succinimidyl carbamate (AQC) (Chapters 4 and 8); (b) 1-fluoro-2,4-
dinitrophenyl-5-L-alanine amide (Marfey’s reagent), which allows separa-
tion and analysis of enantiomeric amino acids (Chapter 5); (c) O-phthalalde-
hyde (OPA) (Chapters 6 and 10); (d) butylisothiocyanate (BITC) and
benzylisothiocyante (BZITC) (Chapter 11); (e) phenylisothiocyanate (PITC)
(Chapters 12 and 13); (f) ammonium-7-fluorobenzo-2-oxa-1,3-diazole-4-sul-
fonate (SBD-F) (Chapter 17); and (g) 9-fluorenylmethyl-chloroformate
(FMOC-Cl) (Chapter 10).
Techniques have been described in which gas chromatography is used to
separate and analyze (a) amino acids after N(O,S)-isoBOC methyl ester
derivatization (Chapter 9); (b) N-isoBOC methyl esters of O-phosphoamino
acids (Chapter 14); and (c) N(S)-isopropoxycarbonyl methyl esters deriva-
tives of sulfur amino acids, glutathione, and other related aminothiols such as
CysGly (Chapter 15). New techniques based on capillary electrophoresis sepa-
ration (Chapter 16), high-performance anion-exchange chromatography (Chap-
ter 7), and mass spectrometry of isotopically labeled proteins (Chapter 18) are
also presented.
v
vi Preface
The applications of amino acid analysis are extremely varied and the
technique remains the best means of accurate protein quantitation. Examples
given in Amino Acid Analysis Protocolsinclude the use of amino acid analysis
for identification of picomolar amounts of protein on PVDF membranes (Chap-
ter 8). The measurements of amino acids in bodily fluids and tissues such as
urine (Chapters 9, 12, 14, 15), blood (Chapters 9, 10, 12, 14, 15, 17), seminal
plasma (Chapter 6), or skeletal muscle tissue (Chapter 16), and measurement
in the presence of high lipid content, such as in porcine lung (Chapter 13), are
useful to help to identify diseases associated with changes in amino acid me-
tabolism. Amino acid analysis, for example, is important to the study of such
disordersas maple syrup urine disease (accumulation of branched-chain L-amino
acids), phenylketonuria (high concentrations of phenylalanine), atherosclerosis
(elevated levels of homocysteine), and galactosemia (often high concentra-
tions of methonine). Amino acid and glucose analysis in fermentation broths of
cell cultures (Chapter 7) enables the development of a feeding strategy that
maintains the correct levels of nutrients. This is important since the use of
such systems to make recombinant products is increasing. A method to deter-
mine the amino acid composition of foods (Chapter 11) is also included.
In addition to the standard methods used to separate the 20 commonly
occurring amino acids, the analysis of unusual and modified amino acids is
also addressed. Specifically, the analysis of homocysteine for monitoring the
development of atherosclerosis (Chapter 17); hydroxyproline, a major amino
acid found in collagen (Chapter 16); phosphoamino acids, which are difficult
because they are acid labile (Chapter 14); aminothiols, such as cysteinylglycine
and cystathionine (Chapter 15); and glycated lysine, implicated in diabetic
complications and Alzheimer’s disease (Chapter 18).
Overall Amino Acid Analysis Protocols presents an up-to-date, detailed
methodology reference for a broad range of current techniques being used for
amino acid analysis.
Catherine Cooper
Nicolle Packer
Keith Williams
Contents
Preface .............................................................................................................v
Contributors.....................................................................................................ix
1 Amino Acid Analysis: An Overview
Margaret I. Tyler.....................................................................................1
2 Amino Acid Analysis, Using Postcolumn Ninhydrin Detection,
in a Biotechnology Laboratory
Frank D. Macchi, Felicity J. Shen, Rodney G. Keck,
and Reed J. Harris.............................................................................9
3 Purification of Proteins Using UltraMacro Spin Columns or ProSorb
Sample Preparation Cartridges for Amino Acid Analysis
Li Zhang and Nancy Denslow............................................................31
4 Amino Acid Analysis Using Precolumn Derivatization
with 6-Aminoquinolyl-N-Hydroxysuccinimidyl Carbamate
Steven A. Cohen..................................................................................39
5 Amino Acid Analysis by High-Performance Liquid Chromatography
after Derivatization with 1-Fluoro-2,4-Dinitrophenyl-5-L-Alanine
Amide (Marfey's Reagent)
Sunil Kochhar, Barbara Mouratou, and Philipp Christen...............49
6 The Analysis of Amino Acids Using Precolumn Derivatization, HPLC,
and Electrochemical Detection
C. David Forster and Charles A. Marsden........................................55
7 Anion Exchange Chromatography and Intergrated Amperometric
Detection of Amino Acids
Petr Jandik, Christopher Pohl, Victor Barreto,
and Nebojsa Avdalovic...................................................................63
8 Ion-Pair Chromatography for Identification of Picomolar-Order
Protein on a PVDF Membrane
Noriko Shindo, Tsutomu Fujimura, Saiko Kazuno,
and Kimie Murayama......................................................................87
vii
viii Contents
9 Capillary Gas Chromatographic Analysis of Protein and Nonprotein
Amino Acids in Biological Samples
Hiroyuki Kataoka, Sayuri Matsumura, Shigeo Yamamoto, and
Masami Makita...............................................................................101
10 Measurement of Blood Plasma Amino Acids in Ultrafiltrates by High-
Performance Liquid Chromatography with Automatic Precolumn
O-Phthaldialdehyde Derivatization
HuaLiu................................................................................................123
11 Determination of Amino Acids in Foods by Reversed-Phase
High-Performance Liquid Chromatography with New Precolumn
Derivatives, Butylthiocarbamyl, and Benzylthiocarbamyl
Derivatives Compared to the Phenylthiocarbamyl Derivative
and Ion Exchange Chromatography
Kang-Lyung Woo...............................................................................141
12 Amino Acid Measurement in Body Fluids Using
PITC Derivatives
Roy A. Sherwood...............................................................................169
13 Determination of Proteins, Phosphatidylethanolamine,
and Phosphatidylserine in Lipid-Rich Materials by Analysis
of Phenylthiocarbamyl Derivatives
Margareta Stark and Jan Johansson..............................................177
14 Analysis of O-Phosphoamino Acids in Biological Samples by Gas
Chromatography with Flame Photometric Detection
Hiroyuki Kataoka, Norihisa Sakiyama, Yukizo Ueno,
Kiyohiko Nakai, and Masami Makita...........................................183
15 Determination of Sulfur Amino Acids, Glutathione, and Related
Aminothiols in Biological Samples by Gas Chromatography
with Flame Photometric Detection
Hiroyuki Kataoka, Kiyomi Takagi, Hirofumi Tanaka,
and Masami Makita........................................................................207
16 Capillary Electrophoretic Determination of 4-Hydroxyproline
Qingyi Chu and Michael Zeece........................................................227
17 Total Plasma Homocysteine Analysis by HPLC with SBD-F
Precolumn Derivatization
Isabella Fermo and Rita Paroni........................................................237
18 Determination of Early Glycation Products by Mass Spectrometry
and Quantification of Glycation Mediated Protein Crosslinks
by the Incorporation of [14C]lysine into Proteins
Malladi Prabhakaram, Beryl J. Ortwerth, and Jean B. Smith.......245
Index............................................................................................................255
Contributors
NEBOJSA AVDALOVIC • Research and Development, Dionex Corporation,
Sunnyvale, CA
VICTOR BARRETO •Research and Development, Dionex Corporation,
Sunnyvale, CA
PHILIPP CHRISTEN, MD• Biochemisches Institut der Universität Zürich,
Zürich, Switzerland
QINGYI CHU • Doheny Eye Institute, Los Angeles, CA
STEVEN A. COHEN• Waters Corporation, Milford, MA
CATHERINE COOPER • Proteome Systems Ltd, North Ryde, Australia
NANCY DENSLOW•Protein Chemistry Core Laboratory, Interdisciplinary
Center for Biotechnology Research (ICBR), University of Florida,
Gainesville, FL
ISABELLA FERMO • Laboratory of Separative Techniques, Department of
Laboratory Medicine, Scientific Institute H. S. Raffaele and School of
Medicine, Milan, Italy
C. DAVID FORSTER • School of Biomedical Sciences, Nottingham University
Medical School, Queen’s Medical Centre, Nottingham, UK
TSUTOMU FUJIMURA • Division of Biochemical Analysis, Central Laboratory
of Medical Sciences, Juntendo University School of Medicine, Tokyo, Japan
REED J. HARRIS•Analytical Chemistry Department, Genentech Inc., San
Francisco, CA
PETR JANDIK • Research and Development, Dionex Corporation,
Sunnyvale, CA
JAN JOHANSSON • Department of Medical Biochemistry and Biophysics,
Karolinska Institutet, Stockholm, Sweden
HIROYUKI KATAOKA • Faculty of Pharmaceutical Sciences, Okayama
University, Okayama, Japan
SAIKO KAZUNO • Division of Biochemical Analysis, Central Laboratory of
Medical Sciences, Juntendo University School of Medicine, Tokyo, Japan
RODNEY G. KECK • Analytical Chemistry Department, Genentech Inc.,
San Francisco, CA
SUNIL KOCHHAR • Department of Bioscience, Nestlé Research Center,
Lausanne, Switzerland
ix