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Cyclic peptides containing a δ-sugar amino acid—synthesis and evaluation as artificial receptors

Billing, Johan LU and Nilsson, Ulf LU (2005) In Tetrahedron 61(4). p.863-874
Abstract
An Fmoc-protected δ-sugar amino acid, prepared by oxidation of a glucosamine derivative, was coupled to three different tripeptide tert-butyl esters (H-Tyr-Tyr-Tyr-OtBu, H-Tyr-Glu(OBzl)-Tyr-OtBu and H-Tyr-Arg(Mtr)-Tyr-OtBu) and the resulting sugar amino acid/amino acid hybrids were transformed into dimers that were subsequently cyclized to give three C2-symmetric macrocycles. The macrocycles were deprotected and their binding properties towards p-nitrophenyl glycosides, nucleotides, and purines were examined. Of the ligands screened, only some of the purines showed weak, but significant, binding.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
artificial receptors, cyclic peptides, sugar amino acids, macrocycles, molecular recognition
in
Tetrahedron
volume
61
issue
4
pages
863 - 874
publisher
Elsevier
external identifiers
  • wos:000226332400011
  • scopus:11144319399
ISSN
0040-4020
DOI
10.1016/j.tet.2004.11.024
language
English
LU publication?
yes
id
3b66f406-5641-4a73-b1e1-7395107ca8e7 (old id 158670)
date added to LUP
2007-07-10 09:17:52
date last changed
2017-08-27 05:13:43
@article{3b66f406-5641-4a73-b1e1-7395107ca8e7,
  abstract     = {An Fmoc-protected δ-sugar amino acid, prepared by oxidation of a glucosamine derivative, was coupled to three different tripeptide tert-butyl esters (H-Tyr-Tyr-Tyr-OtBu, H-Tyr-Glu(OBzl)-Tyr-OtBu and H-Tyr-Arg(Mtr)-Tyr-OtBu) and the resulting sugar amino acid/amino acid hybrids were transformed into dimers that were subsequently cyclized to give three C2-symmetric macrocycles. The macrocycles were deprotected and their binding properties towards p-nitrophenyl glycosides, nucleotides, and purines were examined. Of the ligands screened, only some of the purines showed weak, but significant, binding.},
  author       = {Billing, Johan and Nilsson, Ulf},
  issn         = {0040-4020},
  keyword      = {artificial receptors,cyclic peptides,sugar amino acids,macrocycles,molecular recognition},
  language     = {eng},
  number       = {4},
  pages        = {863--874},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Cyclic peptides containing a δ-sugar amino acid—synthesis and evaluation as artificial receptors},
  url          = {http://dx.doi.org/10.1016/j.tet.2004.11.024},
  volume       = {61},
  year         = {2005},
}