Solid-Phase Synthesis: A Practical Guide

by Albericio; Fernando

• ISBN13: 9780824703592
• ISBN10: 0824703596
• Edition: 1st
• Format: Hardcover
• Copyright: 2000-04-28
• Publisher: CRC Press

Summary

This hands-on reference tool provides the most up-to-date information needed to synthesize molecules by solid-phase synthesis (SPS)-employing polymeric support (resins), anchoring linkages (handles), coupling reagents (activators), and protection schemes. The volume presents new strategies for creating a wide variety of compounds invaluable for drug discovery in coming years. Thoroughly analyzes peptides, DNA, carbohydrates, conjugates of biomolecules, and small molecules. Written by 35 internationally recognized authorities, Solid-Phase Synthesis provides experimental procedures and a literature review for peptides, DNA, PNA, carbohydrates, peptidomimetics, and small molecule assembly describes the preparation of solid supports and handles (linkers) as well as their appropriate incorporation into a synthetic strategy discusses methods for the construction of more complex peptides: cyclic (lactam and disulfide), glyco-, phospho-, sulfo- and nucleopeptides explains the pro

Author Biography

Fernando Albericio: Department of Organic Chemistry, University of Barcelona, Spain Nicholas P. Ambulos, Jr.: Department of Microbiology and Immunology, University of Maryland School of Medicine, Baltimore David Andreu: Department of Organic Chemistry, University of Barcelona, Spain George Barany: Department of Chemistry, University of Minnesota, Minneapolis Laurent Bellon: Department of Oligonucleotide Chemistry, Ribozyme Pharmaceuticals, Inc., Boulder, Colorado Lisa Bibbs: Protein and Nucleic Acids Core Facility, The Scripps Research Institute, La Jolla, California Christopher Blackburn: Drug Discovery, Millennium Pharmaceuticals, Cambridge, Massachusetts Lynda F. Bonewald: Department of Medicine/Endocrinology, The University of Texas Health Science Center at San Antonio Ralph A. Casale: Core PNA Research and Development, PE Biosystems, Framingham, Massachusetts Scott B. Daniels: Instrument Development, PE Biosystems, Framingham, Massachusetts Vern de Biasi: Analytical Sciences, SmithKline Beecham Pharmaceuticals, Essex, England Amanda L. Doherty-Kirby: Department of Chemistry, University of Waterloo, Ontario, Canada Michael Egholm: Core PNA Research and Development, PE Biosystems, Framingham, Massachusetts Ramon Eritja: Instituto de Biologia Molecular de Barcelona, Consejo Superior de Investigaciones Cientificas, Barcelona, Spain Gregg B. Fields: Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton Pilar Forns: Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton Carlos Garcia-Echeverria: Oncology Research, Novartis Pharma Inc., Basel, Switzerland Ernest Giralt: Department of Organic Chemistry, University of Barcelona, Spain Gilles Guichard: Laboratory for Immunological Chemistry, UPR 9021 CNRS, Institut de Biologie Moleculaire et Cellulaire, Strasbourg, France Richard A. Houghten: Department of Chemistry, Torrey Pines Institute for Molecular Studies, San Diego, California Steven A. Kates: Department of Chemistry, Consensus Pharmaceuticals, Inc., Medford, Massachusetts Ashok Khatri: Endocrine Unit/Medicine, Massachusetts General Hospital, Boston Gilles A. Lajoie: Department of Chemistry, University of Waterloo, Ontario, Canada Paul Lloyd-Williams: Department of Organic Chemistry, University of Barcelona, Spain John S. McMurray: Department of Neuro-Oncology, The University of Texas M. D. Anderson Cancer Center, Houston Katalin Folkl Medzihradszky: Department of Pharmaceutical Chemistry, University of California San Francisco Adel Nefzi: Department of Chemistry, Torrey Pines Institute for Molecular Studies, San Diego, California Ernesto Nicolas: Department of Organic Chemistry, University of Barcelona, Spain Andrew Organ: Computational and Structural Sciences, SmithKline Beecham Pharmaceuticals, Essex, England John M. Ostresh: Department of Chemistry, Torrey Pines Institute for Molecular Studies, San Diego, California Jacques Y. Roberge: Early Discovery Chemistry, Bristol-Myers Squibb, Princeton, New Jersey Paolo Rovero: Dipartimento di Scienze Farmaceutiche, Universita di Salerno, Fisciano, Italy John D. Wade: Howard Florey Institute, University of Melbourne, Parkville, Victoria, Australia Susan T. Weintraub: Department of Biochemistry, The University of Texas Health Science Center at San Antonio Francine Wincott: Department of Oligonucleotide Chemistry, Ribozyme Pharmaceuticals, Inc., Boulder, Colorado T. Scott Yokum: Department of Chemistry, University of Minnesota, Minneapolis

Table of Contents

Foreword	iii
R. B. Merrfield
Preface	v
Contributors	xi
Introduction: The Impact of Genome Sequencing on Drug Discovery	xv
Lewis C. Cantley
The Solid Support	1	(78)
Pilar Forns
Gregg B. Fields
Strategy in Solid-Phase Peptide Synthesis	79	(24)
T. Scott Yokum
George Barany
Amino Acids: Alpha-Amino Protecting Groups	103	(26)
John D. Wade
Side-Chain Protecting Groups	129	(68)
Amanda L. Doherty-Kirby
Gilles A. Lajoie
Solid Supports for the Synthesis of Peptides and Small Molecules	197	(78)
Christopher Blackburn
Coupling Methods: Solid-Phase Formation of Amide and Ester Bonds	275	(56)
Fernando Albericio
Steven A. Kates
Homodetic Cyclic Peptides	331	(34)
Paolo Rovero
Disulfide Formation in Synthetic Peptides and Proteins: The State of the Art	365	(12)
David Andreu
Ernesto Nicolas
Solid-Phase Convergent Approaches to the Synthesis of Native Peptides and Proteins	377	(42)
Paul Lloyd-Williams
Ernest Giralt
Preparation of Glyco-, Phospho-, and Sulfopeptides	419	(56)
Carlos Garcia-Echeverria
Oligonucleotide Synthesis	475	(54)
Laurent Bellon
Francine Wincott
Synthesis of Oligonucleotide-Peptide Conjugates and Nucleopeptides	529	(20)
Ramon Eritja
The Chemistry of Peptide Nucleic Acids	549	(30)
Michael Egholm
Ralph A. Casale
Solid-Phase Synthesis of Oligosaccharides	579	(38)
Jacques Y. Roberge
Solid-Phase Synthesis of Heterocyclic Compounds from Amino Acids and Linear Peptides	617	(32)
Adel nefzi
John M. Ostresh
Richard A. Houghten
Solid-Phase Synthesis of Pseudopeptides and Oligomeric Peptide Backbone Mimetics	649	(56)
Gilles Guichard
Instrumentation	705	(30)
Scott B. Daniels
The Purification of Synthetic Peptides	735	(16)
John S. McMurray
Analysis of Synthetic Peptides	751	(40)
Nicholas P. Ambulos, Jr.
Lisa Bibbs
Lynda F. Bonewald
Steven A. Kates
Ashock khatri
Katalin Folkl Medzihradszky
Susan T. Weintraub
The Chromatographic Analysis of Combinatorial Arrays: Parallel HPLC and HPLC-MS	791	(28)
Vern de Biasi
Andrew Organ
Index	819