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Titolo:
APPROACHES TO PSEUDOPEPTIDIC ERGOPEPTINES - SYNTHESIS AND MOLECULAR-STRUCTURE OF AN ALPHA-AZA-PHENYLALANINE-CONTAINING OXA-CYCLOL
Autore:
PINNEN F; LUISI G; LUCENTE G; GAVUZZO E; CERRINI S;
Indirizzi:
UNIV ROMA LA SAPIENZA,DEPT PHARMACEUT STUDIES I-00185 ROME ITALY UNIV ROMA LA SAPIENZA,DEPT PHARMACEUT STUDIES I-00185 ROME ITALY UNIV CATANIA,INST PHARMACEUT CHEM I-95125 CATANIA ITALY CNR,INST STRUCT CHEM G GIACOMELLO I-00016 ROME ITALY
Titolo Testata:
Journal of the Chemical Society. Perkin transactions. I
fascicolo: 7, , anno: 1993,
pagine: 819 - 824
SICI:
0300-922X(1993):7<819:ATPE-S>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
X-RAY; CONFORMATION; PEPTIDE; CRYSTAL; BOND;
Tipo documento:
Article
Natura:
Periodico
Citazioni:
29
Recensione:
Indirizzi per estratti:
Citazione:
F. Pinnen et al., "APPROACHES TO PSEUDOPEPTIDIC ERGOPEPTINES - SYNTHESIS AND MOLECULAR-STRUCTURE OF AN ALPHA-AZA-PHENYLALANINE-CONTAINING OXA-CYCLOL", Journal of the Chemical Society. Perkin transactions. I, (7), 1993, pp. 819-824

Abstract

A synthesis of tetrahedral adduct (oxa-cyclol) 6 structurally relatedto the peptide portion of ergotamine and possessing an alpha-aza-phenylalanine residue in place of the central phenylalanine is described. The reaction sequence comprises acylation of cyclo-(-azaPhe-Pro-) with(S)-2-benzyl-oxypropionyl chloride, followed by chemoselective hydrogenolytic removal of the O-benzyl protecting group. The intermediate N-(alpha-hydroxyacyl)-cyclo-(-azaPhe-Pro-) undergoes spontaneous ring enlargement leading stereospecifically to the tetrahedral adduct 6 tautomeric with the 9-membered cyclodepsitripeptide cyclo-(-Lac-azaPhe-Pro-) 7. The stereochemistry of 6 has been confirmed by an X-ray crystallographic analysis which provides, in addition, detailed information on the structural and conformational features of the newly formed pseudopeptide system.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/09/20 alle ore 16:19:36