Synthesis of 3,4-di-O-acylated glucose-derived furanoid sugar amino acids (Gaa): conformational analysis of a Leu-enkephalin analog containing di-O-myristoylated Gaa

Chakraborty, T. K. ; Krishna Mohan, B. ; Uday Kumar, S. ; Prabhakar, A. ; Jagadeesh, B. (2004) Synthesis of 3,4-di-O-acylated glucose-derived furanoid sugar amino acids (Gaa): conformational analysis of a Leu-enkephalin analog containing di-O-myristoylated Gaa Tetrahedron Letters, 45 (29). pp. 5623-5627. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2004.05.118

Abstract

3,4-Di-O-acylated derivatives 1-3 of a glucose-derived furanoid sugar amino acid (Gaa) were synthesized as novel peptide building blocks to study their effects on peptide conformation. Structural analysis of the di-O-myristoylated Gaa 3-containing Leu-enkephalin analog 4 by various NMR techniques and constrained molecular dynamics (MD) simulation studies established a well-defined β-turn structure in DMSO-d6 with an intramolecular hydrogen bond between PheNH → TyrCO.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Di-O-acylated Furanoid Sugar Amino Acids; Leu-enkephalin; Conformation; NMR
ID Code:20568
Deposited On:20 Nov 2010 14:18
Last Modified:22 May 2011 15:05

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