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Titolo:
GAMMA-TURN CONFORMATION INDUCED BY ALPHA,ALPHA-DISUBSTITUTED AMINO-ACIDS WITH A CYCLIC 6-MEMBERED SIDE-CHAIN
Autore:
PARADISI MP; TORRINI I; ZECCHINI GP; LUCENTE G; GAVUZZO E; MAZZA F; POCHETTI G;
Indirizzi:
UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI FARMACEUT I-00185 ROME ITALY UNIV ROMA LA SAPIENZA,CNR,CTR STUDIO CHIM FARMACO I-00185 ROME ITALY UNIV LAQUILA,DIPARTIMENTO CHIM I-67100 LAQUILA ITALY CNR,IST STRUTTURIST CHIM I-00016 MONTEROTONDO ITALY
Titolo Testata:
Tetrahedron
fascicolo: 8, volume: 51, anno: 1995,
pagine: 2379 - 2386
SICI:
0040-4020(1995)51:8<2379:GCIBAA>2.0.ZU;2-9
Fonte:
ISI
Lingua:
ENG
Soggetto:
CRYSTAL-STRUCTURE; PHE-OME; PEPTIDES; MET;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
18
Recensione:
Indirizzi per estratti:
Citazione:
M.P. Paradisi et al., "GAMMA-TURN CONFORMATION INDUCED BY ALPHA,ALPHA-DISUBSTITUTED AMINO-ACIDS WITH A CYCLIC 6-MEMBERED SIDE-CHAIN", Tetrahedron, 51(8), 1995, pp. 2379-2386

Abstract

4-Aminotetrahydrothiopyran-4-carboxylic acid (Thp) is an unusual achiral cyclic alpha,alpha-disubstituted amino acid mimicking the natural Met residue. The conformational energy map computed for Ac-Thp-NHMe shows that the gamma-turn is the lowest minimum. H-1-NMR and IR studies performed on For-Thp-Leu-OMe (2a), a short peptide unable to give a 4...>1 H-bond, indicate that the gamma-turn is adopted in CDCl3 solution, whereas is not retained in(CD3)(2)SO. An analogous conformational behaviour in solution has been observed for the strictly related For-Ac(6)c-Leu-OMe (2b), containing 1-aminocyclohexane carboxylic acid (Ac(6)c).

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Documento generato il 22/09/20 alle ore 15:57:56