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Cyclization of Linear Tetrapeptides Containing N ‐Methylated Amino Acids by using 1‐Propanephosphonic Acid Anhydride
Author(s) -
Zhang Shengping,
De Leon Rodriguez Luis M.,
Lacey Ernest,
Piggott Andrew M.,
Leung Ivanhoe K. H.,
Brimble Margaret A.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601016
Subject(s) - chemistry , conformational isomerism , stereochemistry , hydrolysis , sequence (biology) , amino acid , organic chemistry , molecule , biochemistry
The cyclization of the linear tetrapeptides sequence H‐ N MePhe‐Xaa 1 ‐ N MePhe‐Xaa 2 ‐OH (for which Xaa 1 = Xaa 2 = Ile, Val, or Leu; Xaa 1 = Val; Xaa 2 = Ile or Leu) by using 1‐propanephosphonic acid anhydride was explored. An unanticipated finding is the cyclization towards cyclotetrapeptide conformers (kinetic products) that were highly prone to hydrolysis and that slowly interconvert into the more stable trans , cis , trans , cis ( tctc ) conformers (thermodynamic products).