Cyclic peptides containing a δ-sugar amino acid—synthesis and evaluation as artificial receptors
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/158670
- author
- Billing, Johan LU and Nilsson, Ulf LU
- organization
- publishing date
- 2005
- 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
- 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
- 3b66f406-5641-4a73-b1e1-7395107ca8e7 (old id 158670)
- date added to LUP
- 2016-04-01 15:48:51
- date last changed
- 2022-01-28 07:16:52
@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}}, keywords = {{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}}, doi = {{10.1016/j.tet.2004.11.024}}, volume = {{61}}, year = {{2005}}, }