Total synthesis, structure, and oral absorption of a thiazole cyclic peptide, sanguinamide A

Nielsen, Daniel S., Hoang, Huy N., Lohman, Rink-Jan, Diness, Frederik and Fairlie, David P. (2013) Total synthesis, structure, and oral absorption of a thiazole cyclic peptide, sanguinamide A. Organic Letters, 14 22: 5720-5723. doi:10.1021/ol3027347


Author Nielsen, Daniel S.
Hoang, Huy N.
Lohman, Rink-Jan
Diness, Frederik
Fairlie, David P.
Title Total synthesis, structure, and oral absorption of a thiazole cyclic peptide, sanguinamide A
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
1523-7052
Publication date 2013
Year available 2012
Sub-type Article (original research)
DOI 10.1021/ol3027347
Volume 14
Issue 22
Start page 5720
End page 5723
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2013
Language eng
Formatted 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.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Publication Date (Web): November 6, 2012

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Institute for Molecular Bioscience - Publications
 
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Created: Wed, 14 Nov 2012, 13:09:09 EST by Susan Allen on behalf of Institute for Molecular Bioscience