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Titolo:
Conformational study and enantioselective, regiospecific syntheses of novel aminoxy trans-proline analogues derived from an acylnitroso Diels-Alder cycloaddition
Autore:
Shireman, BT; Miller, MJ; Jonas, M; Wiest, O;
Indirizzi:
Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA Univ Notre Dame Notre Dame IN USA 46556 Biochem, Notre Dame, IN 46556 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 18, volume: 66, anno: 2001,
pagine: 6046 - 6056
SICI:
0022-3263(20010907)66:18<6046:CSAERS>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-HAIRPIN FORMATION; PEPTIDE-BOND ISOMERIZATION; ACYL NITROSO-COMPOUNDS; XXX-L-PRO; N-O BOND; SECONDARY STRUCTURES; ASYMMETRIC-SYNTHESIS; AQUEOUS-SOLUTION; HYDROGEN-BOND; ACID;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
99
Recensione:
Indirizzi per estratti:
Indirizzo: Miller, MJ Univ Notre Dame, Dept Chem & Biochem, 251 Nieuwland Sci Hall, Notre Dame, IN 46556 USA Univ Notre Dame 251 Nieuwland Sci Hall Notre Dame IN USA 46556
Citazione:
B.T. Shireman et al., "Conformational study and enantioselective, regiospecific syntheses of novel aminoxy trans-proline analogues derived from an acylnitroso Diels-Alder cycloaddition", J ORG CHEM, 66(18), 2001, pp. 6046-6056

Abstract

The cis/trans isomerization of the proline amide bond has many implications in biological processes. The conformations of representative acylnitroso-derived proline analogues derived from cyclopentadiene were shown to exist exclusively as the E or trans conformation in CD2Cl2. The energetically favored conformations were determined using COSMO self-consistent reaction field calculations at the B3LYP/6-31G* level of theory in addition to low temperature H-1 NMR studies. The syntheses of the acylnitroso-derived peptides utilized two methods to selectively functionalize either of two chemically similar esters in the acylnitroso-derived amino acids. A novel transpeptidation of the amino acid that controlled the absolute stereochemistry in the acylnitroso Diels-Alder cycloaddition took advantage of an activated aminoxy amide linkage to control regiochemistry. Alternatively, an enantioselective and regiospecific enzymatic resolution of a racemic dimethyl ester provided a novel aminoxy acid.

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Documento generato il 04/12/20 alle ore 16:29:24