Efficient, Racemization-Free Peptide Coupling of N-Alkyl Amino Acids by Using Amino Acid Chlorides Generated In Situ-Total Syntheses of the Cyclopeptides Cyclosporin O and Omphalotin A

An efficient coupling reaction in peptide chemistry is achieved through the use of Fmoc‐protected amino acid chlorides generated in situ. This method permits racemization‐free incorporation of N‐methyl amino acids into peptides, as could be shown in the syntheses of cyclosporin O (1) and omphalotin...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2002-12, Vol.41 (24), p.4661-4663
Main Author: Sewald, Norbert
Format: Article
Language:English
Subjects:
Amino Acid Sequence
amino acids
Amino Acids - chemistry
bioorganic chemistry
Chlorides - chemistry
coupling reagent
Cyclosporins - chemical synthesis
Cyclosporins - chemistry
Isomerism
peptides
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Protein Conformation
total synthesis
triphosgene
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Summary:An efficient coupling reaction in peptide chemistry is achieved through the use of Fmoc‐protected amino acid chlorides generated in situ. This method permits racemization‐free incorporation of N‐methyl amino acids into peptides, as could be shown in the syntheses of cyclosporin O (1) and omphalotin A.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200290008