Cyclization of Linear Tetrapeptides Containing N‐Methylated Amino Acids by using 1‐Propanephosphonic Acid Anhydride. Issue 1 (5th December 2016)

• Record Type: Journal Article
• Authors: Zhang, Shengping; De Leon Rodriguez, Luis M.; Lacey, Ernest; Piggott, Andrew M.; Leung, Ivanhoe K. H.; Brimble, Margaret A.
• Is Part Of: European journal of organic chemistry. Issue 1(2017)
• Page Start: 149
• Page End: 158
• Publication Date: 2016-12-05
• Subjects: Cyclization -- Tetrapeptides -- Conformation analysis -- Natural products -- Biological activity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601016
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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). Abstract : The synthesis of a series of naturally occurring cyclotetrapeptides and an analogue with 1‐propanephosphonic acid anhydride (T3P) is reported. An unexpected finding is the formation of unstable cyclic peptide conformers in addition to the more stable trans, cis, trans, cis ( tctc ) cyclopeptides.