Total Synthesis, Structure, and Oral Absorption of a Thiazole Cyclic Peptide, Sanguinamide A
Organic Letters2012Vol. 14(22), pp. 5720–5723
Citations Over TimeTop 10% of 2012 papers
Abstract
The first total synthesis and three-dimensional solution structure are reported for sanguinamide A, a thiazole-containing cyclic peptide from the sea slug H. sanguineus. Solution phase fragment synthesis, solid phase fragment assembly, and solution macrocyclization were combined to give (1) in 10% yield. Spectral properties were identical for the natural product, requiring revision of its structure from (2) to (1). Intramolecular transannular hydrogen bonds help to bury polar atoms, which enables oral absorption from the gut.
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