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Synthesis and conformational studies of a Leu-enkephalin amide analogue containing a ferrocene substructure

Maricic, Suzana LU ; Berg, Ulf LU and Frejd, Torbjörn LU (2002) In Tetrahedron 58(15). p.3085-3093
Abstract
Solution phase synthesis of a constrained Leu(5)-enkephalin amide analogue 10 is reported, in which the cyclic ferrocenyl containing subunit 7 was introduced as a mimetic of the tetrapeptide Tyr-Gly-Gly-Phe unit. Temperature dependence of the chemical shift of the amide protons of 10 indicated a hydrogen bond between the same amino acid residues as observed for the natural Leu-enkepalin in the single-bend conformation. The rotational barrier (DeltaG(c)(not equal)=16.8 kcal/mol) of the C-terminal amide group, which was determined by DNMR spectroscopy, and NOESY experiments indicated that the two termini were more distant as compared to the single-bend conformation of natural Leu-enkephalin amide. (C) 2002 Elsevier Science Ltd. All rights... (More)
Solution phase synthesis of a constrained Leu(5)-enkephalin amide analogue 10 is reported, in which the cyclic ferrocenyl containing subunit 7 was introduced as a mimetic of the tetrapeptide Tyr-Gly-Gly-Phe unit. Temperature dependence of the chemical shift of the amide protons of 10 indicated a hydrogen bond between the same amino acid residues as observed for the natural Leu-enkepalin in the single-bend conformation. The rotational barrier (DeltaG(c)(not equal)=16.8 kcal/mol) of the C-terminal amide group, which was determined by DNMR spectroscopy, and NOESY experiments indicated that the two termini were more distant as compared to the single-bend conformation of natural Leu-enkephalin amide. (C) 2002 Elsevier Science Ltd. All rights reserved. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
conformational analysis, ferrocene, cyclic peptide, beta-turn mimetic
in
Tetrahedron
volume
58
issue
15
pages
3085 - 3093
publisher
Elsevier
external identifiers
  • wos:000175580900021
  • scopus:0037041519
ISSN
0040-4020
DOI
10.1016/S0040-4020(02)00170-9
language
English
LU publication?
yes
id
dda22871-d2cb-4baf-b1e7-780706ef6f3f (old id 337375)
date added to LUP
2007-11-19 13:48:48
date last changed
2017-08-13 04:26:32
@article{dda22871-d2cb-4baf-b1e7-780706ef6f3f,
  abstract     = {Solution phase synthesis of a constrained Leu(5)-enkephalin amide analogue 10 is reported, in which the cyclic ferrocenyl containing subunit 7 was introduced as a mimetic of the tetrapeptide Tyr-Gly-Gly-Phe unit. Temperature dependence of the chemical shift of the amide protons of 10 indicated a hydrogen bond between the same amino acid residues as observed for the natural Leu-enkepalin in the single-bend conformation. The rotational barrier (DeltaG(c)(not equal)=16.8 kcal/mol) of the C-terminal amide group, which was determined by DNMR spectroscopy, and NOESY experiments indicated that the two termini were more distant as compared to the single-bend conformation of natural Leu-enkephalin amide. (C) 2002 Elsevier Science Ltd. All rights reserved.},
  author       = {Maricic, Suzana and Berg, Ulf and Frejd, Torbjörn},
  issn         = {0040-4020},
  keyword      = {conformational analysis,ferrocene,cyclic peptide,beta-turn mimetic},
  language     = {eng},
  number       = {15},
  pages        = {3085--3093},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Synthesis and conformational studies of a Leu-enkephalin amide analogue containing a ferrocene substructure},
  url          = {http://dx.doi.org/10.1016/S0040-4020(02)00170-9},
  volume       = {58},
  year         = {2002},
}