Synthesis and conformational studies of a Leu-enkephalin amide analogue containing a ferrocene substructure
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/337375
- author
- Maricic, Suzana LU ; Berg, Ulf LU and Frejd, Torbjörn LU
- organization
- publishing date
- 2002
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- dda22871-d2cb-4baf-b1e7-780706ef6f3f (old id 337375)
- date added to LUP
- 2016-04-01 16:42:55
- date last changed
- 2022-02-27 23:06:27
@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}},
keywords = {{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}},
doi = {{10.1016/S0040-4020(02)00170-9}},
volume = {{58}},
year = {{2002}},
}