d-Amino Acids in Sequences of Secreted Peptides of Multicellular Organisms

190 Pages·1998·7.02 MB·English

by  P. Jollès (ed.)

EXS 85
D-Amino Acids in Sequences
of Secreted Peptides
of Multicellular Organisms
Edited by P. J ol1es
Springer Basel AG
Editor
Prof. Dr. P. Jolles
Laboratoire de Chimie
des Substances Naturelles
URA C.N.R.S. No. 401
Museum National d'Histoire Naturelle
63, rue Buffon
F-75005 Paris
France
Library of Congress Cataloging-in-Publication Data
D-amino acids in sequences of secreted peptides of multicellular
organisms / edited by P. Jolles.
p. cm. --(EXS ; 85)
Includes bibliographical references and index.
ISBN 978-3-0348-9794-5 ISBN 978-3-0348-8837-0 (eBook)
DOI 10.1007/978-3-0348-8837-0
1. Post-translational modification. 2. Enantiomers. 3. Amino
acids. 4. Peptides. I. Jolles. Pierre, 1927- . II. Series.
QH450.6.D14 1998
572' .633--dc21
Deutsche Bibliothek Cataloging-in-Publication Data
D-amino acids in sequences of secreted peptides of multicellular
organisms / ed. by P. Jolles. -Basel ; Boston; Berlin: Birkhiiuser, 1998
(EXS; 85)
ISBN 978-3-0348-9794-5
EXS. -Basel ; Boston; Berlin: Birkhiiuser
Friiher Schriftenreihe
Fortlaufende BeiI. zu: Experientia
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© 1998 Springer Basel AG
Origina1ly published by Birkhiluser Verlag in 1998
Softcover reprint of the hardcover Ist edition 1998
Printed on acid-free paper produced from chlorine-free pulp.TCF
00
ISBN 978-3-0348-9794-5
987654321
Contents
List of Contributors VII
Preface IX
0 0 0 0 0 0 0
Characterization and analysis of D-amino acids
Ao Scaloni, Mo Simmaco and F Bossa
Characterization and analysis of D-amino acids 3
Occurence and function of D-amino acids-containing peptides
and proteins
Go Mignogna, Mo Simmaco and Do Barra
Occurrence and function of D-amino acids-containing peptides
and proteins: Antimicrobial peptides 29
0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Y. Yasuda-Kamatani
Molluscan neuropeptides 37
0
M. Amiche, Ao Delfour and P. Nicolas
Opioid peptides from frog skin 57
0
Ao Huberman and M. Bo Aguilar
D-Amino acids in crustacean hyperglycemic neurohormones 73
Biosynthesis: A new family of isomerases
s.D.
RoAo Volkmann and Heck
Biosynthesis of D-amino acid-containing peptides:
Exploring the role of peptide isomerases 87
0 0 0 0
Appearance of D-amino acids during aging
GoH. Fisher
Appearance of D-amino acids during aging:
D-Amino acids in tumor proteins 109
0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Do Ingrosso andAoF Perna
D-Amino acids in aging erythrocytes 119
0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
VI Contents
o-Amino acids hydrolysing enzymes
R. Yamada and Y. Kera
o-Amino acid hydrolysing enzymes ................... 145
Homochirality and life
W.A. Bonner
Homochirality and life . . . . . . . . . . . . . . . . . . . . . . . . . . 159
Subject index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189
List of Contributors
M. Amiche, Laboratoire de Bioactivation des Peptides, Institut Jacques Monod,
Universite Paris 7, 2 Place Jussieu, F-75251 Paris Cedex 05, France
D. Barra, Istituto Pasteur-Fondazione Cenci Bolognetti, Dipartimento di
Scienze Biochimiche "A. Rossi Fanelli" and CNR Centro di Biologia Mole
colare, Universita La Sapienza, PiazzaleAldo Moro 5, 1-00185 Roma, Italy
W A. Bonner, Department of Chemistry, Stanford University, Stanford, CA
94305, USA
F. Bossa, Dipartimento di Scienze Biochimiche "A. Rossi Fanelli" and CNR
Centro di Biologia Molecolare, Universita La Sapienza, Piazzale Aldo
Moro 5, 1-00185 Roma, Italy
A. Delfour, Laboratoire de Bioactivation des Peptides, Institut Jacques Monod,
Universite Paris 7, 2 Place Jussieu, F-75251 Paris Cedex 05, France
G. H. Fisher, Department of Chemistry, Barry University, 11300 Northeast
Second Avenue, Miami, FL 33161-6695, USA
S. D. Heck, pfizer Central Research, Eastern Point Road, Groton, CT 06340,
USA
A. Huberman, Department of Biochemistry, Inst. Nac. de la Nutrici6n "Salva
dor Zubinin", Vasco de Quiroga 15, Tlalpan, Mexico City 14000, Mexico
D. Ingrosso, Institute of Biochemistry of Macromolecules, S. U. N. School of
Medicine and Surgery, Via Constantinopoli 16,1-80138 Naples, Italy
Y. Kera, Department of Environmental Systems Engineering, Nagaoka Uni
versity of Technology, Nagaoka, Niigata 940-21, Japan
G. Mignogna, Istituto Pasteur-Fondazione Cenci Bolognetti, Dipartimento di
Scienze Biochimiche "A. Rossi Fanelli" and CNR Centro di Biologia Mole
colare, Universita La Sapienza, PiazzaleAldo Moro 5, 1-00185 Roma, Italy
P. Nicolas, Laboratoire de Bioactivation des Peptides, Institut Jacques Monod,
Universite Paris 7, 2 Place Jussieu, F-75251 Paris Cedex 05, France
A. F. Perna, Institute of Biochemistry of Macromolecules, S. U. N. School of
Medicine and Surgery, Via Constantinopoli 16,1-80138 Naples, Italy
VIII List of Contributors
A. Scaloni, Centro Internazionale di Servizi di Spettrometria di Massa
IABBAM, Consiglio Nazionale delle Ricerche, Via Pansini, 1-80137 Napoli,
Italy
M. Simmaco, Dipartimento di Scienze Biomediche, Universita di Chieti G.
D' Annunzio, Via dei Vestini, 1-66100 Chieti, Italy
R. A. Volkmann, Pfizer Central Research, Eastern Point Road, Groton, CT
06340, USA
R. Yamada, Department of Environmental Systems Engineering, Nagaoka
University of Technology, Nagaoka, Niigata 940-21, Japan
Y. Yasuda-Kamatani, Suntory Institute for Bioorganic Research, 1-1-1 Waka
yamadai, Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan
Preface
Proteins are synthesized on polysomes as simple chains of L-amino acids.
They can later be modified through numerous types of post-translational reac
tions. In fact, practically all their reactive groups can be modified in vivo by
various enzymatic or chemical reactions. After the addition of carbohydrates,
lipids, sulfate or phosphate groups, the properties of the primary products are
changed in many regards, for example, with respect to solubility, stability,
interactions of the proteins with receptor molecules, as well as catalytic and
biological activities.
Recently, a new type of post-translational reaction has been described in
sequences of peptides of multicellular organisms: the conversion of certain
amino acids in peptide links from L- to D-configuration. This modification is
quite subtle; as it cannot be detected by standard amino acid sequencing tech
niques and does not lead to a ~hange in the molecular mass it can take place
unnoticed.
It seems appropriate at this stage to summarize our current knowledge con
cerning the occurrence, the function and the biosynthesis of the D-amino acid
containing peptides in multicellular organisms.
I sincerely thank the authors, all of them well-known experts in the field, for
contributing incisive chapters to this book. The danger of redundancy is often
present in works authored collectively. We have tried hard to minimize the
problem as much as possible.
Pierre Jolles
Paris, February 1998
Characterization and analysis
of D-amino acids