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Synthesis and conformational analysis of optically active ferrocene containing macrocyclic peptides

Maricic, Suzana LU and Frejd, Torbjörn LU (2002) In Journal of Organic Chemistry 67(22). p.7600-7606
Abstract
Two macrocyclic peptides 3 and 4 were formed during lactamization of 1,1'-ferrocenylbis(alanine) 1. Isolation, structure determination, and conformational analysis of 3 and 4 are reported as well as a controlled stepwise synthesis of 4 also including an improved route to 1. On the basis of their H-1 NMR spectra recorded at 300 K in DMSO-d(6), the dimer 3 and trimer 4 were found to be C-2 and C-3 symmetric, respectively. As appeared from computational analysis, the low-energy conformations of the macrocyclic peptides were nonsymmetric. Cyclic voltammetry revealed that the ferrocenyl moieties in 3 or 4 are electrochemically equal to ferrocene.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
67
issue
22
pages
7600 - 7606
publisher
The American Chemical Society
external identifiers
  • pmid:12398478
  • wos:000178820200003
  • scopus:0036827599
ISSN
1520-6904
DOI
10.1021/jo020353b
language
English
LU publication?
yes
id
5555daa0-403a-410b-bd92-6fba23879c82 (old id 324727)
date added to LUP
2007-11-19 13:34:04
date last changed
2017-12-10 03:56:19
@article{5555daa0-403a-410b-bd92-6fba23879c82,
  abstract     = {Two macrocyclic peptides 3 and 4 were formed during lactamization of 1,1'-ferrocenylbis(alanine) 1. Isolation, structure determination, and conformational analysis of 3 and 4 are reported as well as a controlled stepwise synthesis of 4 also including an improved route to 1. On the basis of their H-1 NMR spectra recorded at 300 K in DMSO-d(6), the dimer 3 and trimer 4 were found to be C-2 and C-3 symmetric, respectively. As appeared from computational analysis, the low-energy conformations of the macrocyclic peptides were nonsymmetric. Cyclic voltammetry revealed that the ferrocenyl moieties in 3 or 4 are electrochemically equal to ferrocene.},
  author       = {Maricic, Suzana and Frejd, Torbjörn},
  issn         = {1520-6904},
  language     = {eng},
  number       = {22},
  pages        = {7600--7606},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Synthesis and conformational analysis of optically active ferrocene containing macrocyclic peptides},
  url          = {http://dx.doi.org/10.1021/jo020353b},
  volume       = {67},
  year         = {2002},
}