Peptides

Proceedings of the Sixth European Symposium, Athens, September 1963

L. Zervas

• Publisher: Pergamon
• Year: 2014
• Print ISBN:
  9781483198514
• eBook ISBN:
  9781483223544
• Topic: Physical Sciences
• Subtopic: Biophysics

Peptides covers the proceedings of the Sixth European Peptide Symposium, held in Athens, Greece on September 1963. This symposium brings together numerous works on the synthesis, reactions, biological activity, and physico-chemical properties of peptides. This book is organized into seven sections encompassing 46 chapters. The first three sections describe the methods of peptide synthesis, racemization, and degradation of peptide chains. These sections examine the developments in non-enzymatic selective modification and cleavage of peptides, as well as the oxidative modification of specific peptide chain. The succeeding section highlights the total synthesis of natural peptides and peptide analogues and the evaluation of the structure-activity relationships and biological properties of these peptides. These topics are followed by discussions on the synthetic pathways and properties of certain special peptides, along with the accompanying synthesis problems with uncommon amino acids and abnormal peptides. This final section explores the gas-chromatographic studies on the physic-chemical properties of peptides. This book will prove useful to organic chemists, biochemists, and peptide researchers.

SECTION I

METHODS OF SYNTHESIS

Outline

Chapter 1: SYNTHESIS OF ARGINYL PEPTIDES THROUGH ORNITHYL PEPTIDES

Chapter 2: USE OF THE S-ETHYLCARBAMOYL GROUP FOR PROTECTION OF THE THIOL FUNCTION OF CYSTEINE

Chapter 3: FISSION OF TOSYLAMIDE GROUPS WITH METALS IN LIQUID AMMONIA

Chapter 4: REDUCTION OF NITROARGININE DERIVATIVES: INTERMEDIATES AND SIDE REACTIONS

Chapter 5: ÜBER DEN SCHUTZ DER HYDROXYLGRUPPE DES SERINS MIT DEM p-CHLORBENZYL-RADIKAL

Chapter 6: CHROMOGENIC ACID-LABILE PROTECTING GROUPS FOR USE IN PEPTIDE SYNTHESIS

Chapter 7: SYNTHESE VON POLYPEPTIDEN OHNE ISOLIERUNG DER ZWISCHENPRODUKTE

Chapter 8: KERNSUBSTITUIERTE CARBOBENZOXY-SCHUTZGRUPPEN. VERGLEICHENDE UNTERSUCHUNG DER ACIDOLYTISCHEN SPALTUNG

Chapter 9: CYCLISIERUNG VON PEPTIDEN, BESONDERS AN THIOÄTHERN

Chapter 10: DIE AKTIVIERUNG VON ACYLAMINOSÄUREN UND ACYLPEPTIDEN MIT DICYCLOHEXYLCARBODIIMID

Chapter 11: ZUR SYNTHESE VON HYDROXYAMINOSÄUREPEPTIDEN

Chapter 12: CATALYSIS OF PEPTIDE SYNTHESIS. FACILITATION OF ESTER AMINOLYSIS BY BIFUNCTIONAL CATALYSTS VIA A CONCERTED DISPLACEMENT

Chapter 13: PEPTIDSYNTHESEN MIT HILFE VON PROTEOLYTISCHEN ENZYMEN (PLASTEINREAKTION)

Chapter 14: SYNTHESIS AND SOME PROPERTIES OF DISERYLPYROPHOSPHATES

Chapter 15: THE PARTICIPATION OF THE AMIDE GROUP IN THE SOLVOLYSIS OF PHOSPHORIC ACID TRIESTERS DERIVED FROM SERINE AND ETHANOLAMINE

Chapter 16: NEW METHODS IN PEPTIDE SYNTHESIS

Chapter 17: DISCUSSION ON METHODS OF SYNTHESIS

SYNTHESIS OF ARGINYL PEPTIDES THROUGH ORNITHYL PEPTIDES

M. BODANSZKY, C.A. BIRKHIMER, S. LANDE, M.A. ONDETTI, J.T. SHEEHAN and N.J. WILLIAMS, The Squibb Institute for Medical Research, New Brunswick, N. J.

Publisher Summary

This chapter discusses the synthesis of arginyl peptides through ornithyl peptides. One of the problems in the application of derivatives of ornithine in peptide synthesis is the extreme ease with which most of them cyclize to a lactam. The active ester p-nitrophenyl α-benzyloxycarbonyl-δ-phthalyl-L-ornithinate (I) is prepared by phthalylation of the copper complex of L-ornithine with Nefkens’ reagent followed by carbobenzyloxylation and finally conversion to the p-nitrophenyl ester. Three biologically active arginine-containing peptides can be selected as models for the synthetic approach, namely, arginine vasopressin, arginine vasotocin, and the shortest sequence of α-MSH, or of ACTH, which shows melanocyte stimulating activity, namely, histidyl-phenyl-alanyl-arginyl-tryptophyl-glycine. In the synthesis of the pituitary hormones, the active ester I is allowed to react with glycinamide, the resulting protected dipeptide is treated with HBr in acetic acid. For the removal of the phthalyl group, hydrazine can be added to the solution of the protected nonapeptides in dimethylformamide, while a mixture of methanol and chloroform can be used as a solvent in the case of the protected pentapeptide.

THE difficulties in the synthesis of arginine-containing peptides are well known [1] and although there are several methods which solve this problem, even the one mo...

Table of contents

• Cover image
• Title page
• Table of Contents
• Copyright
• PREFACE
• LIST OF PARTICIPANTS
• ABBREVIATIONS
• SECTION I: METHODS OF SYNTHESIS
• SECTION II: RACEMIZATION
• SECTION III: DEGRADATION OF PEPTIDE CHAINS
• SECTION IV: SYNTHESIS OF NATURAL POLYPEPTIDES AND ANALOGUES. CHEMICAL STRUCTURE AND BIOLOGICAL ACTIVITY
• SECTION V: SYNTHESIS AND PROPERTIES OF SOME SPECIAL PEPTIDES
• SECTION VI: SPECIAL PROBLEMS WITH UNCOMMON AMINO-ACIDS. ABNORMAL PEPTIDES
• SECTION VII: CHEMICAL AND PHYSICAL PROPERTIES OF PEPTIDES