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Cyclic peptides containing a δ-sugar amino acid—synthesis and evaluation as artificial receptors
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- Billing, Johan (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Nilsson, Ulf (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
- (creator_code:org_t)
- Elsevier BV, 2005
- 2005
- English.
- In: Tetrahedron. - : Elsevier BV. - 0040-4020. ; 61:4, s. 863-874
- Journal article (peer-reviewed)
Abstract
Subject headings
Close
- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- artificial receptors
- cyclic peptides
- sugar amino acids
- macrocycles
- molecular recognition
Publication and Content Type
- art (subject category)
- ref (subject category)
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