Self-condensation of a thiazole-peptide bearing a 21-membered loop into a library of giant macrocycles with multiple orthogonal loops

Singh, Y, Hoang, HN, Flanagan, B and Fairlie, DP (2006) Self-condensation of a thiazole-peptide bearing a 21-membered loop into a library of giant macrocycles with multiple orthogonal loops. Organic Letters, 8 6: 1053-1056. doi:10.1021/ol052842e


Author Singh, Y
Hoang, HN
Flanagan, B
Fairlie, DP
Title Self-condensation of a thiazole-peptide bearing a 21-membered loop into a library of giant macrocycles with multiple orthogonal loops
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
Publication date 2006-01-01
Sub-type Article (original research)
DOI 10.1021/ol052842e
Volume 8
Issue 6
Start page 1053
End page 1056
Total pages 4
Editor Amos B. Smith
III
Place of publication Washington
Publisher American Chemical Society
Language eng
Subject C1
250301 Organic Chemical Synthesis
780103 Chemical sciences
Abstract Tetrapeptide analogue H-[Glu-Ser-Lys(Thz)]-OH, containing a turn-inducing thiazole constraint, was used as a template to produce a 21-membered structurally characterized loop by linking Glu and Lys side chains with a Val-Ile dipeptide. This template was oligomerized in one pot to a library (cyclo-[1](n), n = 2-10) of giant symmetrical macrocycles (up to 120-membered rings), fused to 2-10 appended loops that were carried intact through multiple oligomerization (chain extension) and cyclization (chain terminating) reactions of the template. A three-dimensional solution structure for cyclo-[1](3) shows all three appended loops projecting from the same face of the macrocycle. This is a promising approach to separating pepticle motifs over large distances.
Keyword Chemistry, Organic
Amino-acids
Cyclooligomerization
Conformations
Proteins
Q-Index Code C1

 
Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 1 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 1 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Wed, 15 Aug 2007, 19:13:05 EST