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A method for the facile solid-phase synthesis of gramicidin S and its analogs

✍ Scribed by David S. Wishart; Leslie H. Kondejewski; Paul D. Semchuk; Brian D. Sykes; Robert S. Hodges

Publisher
Springer Netherlands
Year
1996
Tongue
English
Weight
489 KB
Volume
3
Category
Article
ISSN
1573-3149

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✦ Synopsis

A simple method is described for the facile synthesis of gramicidin S and six other analogs, using standard solidphase synthetic technology and a single solution-phase cyclization step. The peptides were purified to homogeneity and characterized by plasma desorption time-of-flight mass spectrometry and NMR spectroscopy. Complete ~H NMR assignments for all seven peptides (in aqueous solution) are presented. Unlike previous approaches, the presented method is simple, automatable, rapid (less than three days), high-yielding, requires no side-chain protection during cyclization, and appears to be generally applicable to the preparation of a variety of related head-to-tail cyclic peptides.

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