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Synthesis 1974; 1974(8): 549-559
DOI: 10.1055/s-1974-23365
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The Azide Method in Peptide Synthesis: Its Scope and Limitations1

Yakir S. KLAUSNER* , Miklos BODANSZKY
  • *Department of Biological Chemistry, the Hebrew University, Jerusalem, Israel and Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, U.S.A.
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Publication Date:
12 September 2002 (online)

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The chemistry, scope, and limitations of the azide method of peptide synthesis are discussed with special emphasis on side reactions encountered during the preparation of hydrazides, azides, and in the coupling process. Curtius rearrangement, racemization, and amide formation are part of the discussion. 1. The Formation of Hydrazides 2. Side Reactions in the Preparation of Hydrazides 3. The Preparation of Azides from Hydrazides 4. Side Reactions during Azide Formation 5. Acylation with Azides 6. Side Reactions in Azide Coupling 7. Modifications of the Azide Method 7.1. The Honzl-Rudinger Method 7.2. The Medzihradszky Method 8. Racemization in Coupling with Azides 9. The Azide Method in Solid-Phase Peptide Synthesis 9.1. The Preparation of Peptide Hydrazides 9.2. The Building of Peptide Chains 10. Cyclization with the Azide Method 11. Polymerization by the Azide Method 12. Acyldiimides