Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
VERSATILE SYNTHON FOR CHIRALLY BETA-DEUTERATED L-AMINO-ACIDS AND SYNTHESIS OF (3R)-[3-H-2(1)]-L-SERINE AND (3S)-[3-H-2(1)]-L-SERINE
Autore:
MAEDA Y; TAGO K; EGUCHI T; KAKINUMA K;
Indirizzi:
TOKYO INST TECHNOL,DEPT CHEM,MEGURO KU TOKYO 152 JAPAN TOKYO INST TECHNOL,DEPT CHEM,MEGURO KU TOKYO 152 JAPAN
Titolo Testata:
Bioscience, biotechnology, and biochemistry
fascicolo: 8, volume: 60, anno: 1996,
pagine: 1248 - 1254
SICI:
0916-8451(1996)60:8<1248:VSFCBL>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
D-GLUCOSE; 3-ISOPROPYLMALATE DEHYDROGENASE; TEMPLATE; REARRANGEMENT;
Keywords:
SYNTHESIS; CHIRAL LABELING; AMINO ACID; CHIRALITY TEMPLATE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
16
Recensione:
Indirizzi per estratti:
Citazione:
Y. Maeda et al., "VERSATILE SYNTHON FOR CHIRALLY BETA-DEUTERATED L-AMINO-ACIDS AND SYNTHESIS OF (3R)-[3-H-2(1)]-L-SERINE AND (3S)-[3-H-2(1)]-L-SERINE", Bioscience, biotechnology, and biochemistry, 60(8), 1996, pp. 1248-1254

Abstract

A divergent and highly enantioselective synthetic methodology for producing chirally beta-deuterated L-amino acids was developed. This method is based upon the chirality transcription approach, using diacetone-D-glucos-3-ulose (1) as a template. (N-benzyl)methylthioformimidoyl-D-allo-derivatives (3b and 3c), which are easily accessible from 1, were subjected to halonium ion-assisted cyclization to afford highly diastereoselectively and efficiently versatile 5-membered cyclic carbamatesynthons having a stereochemically defined deuterated halomethyl group (4c and 4d, respectively). Subsequent straightforward transformationof these synthons gave rise to (3R)- and (3S)-[3-H-2(1)]-L-serine. Further transformation of the crucial halomethyl group of 4a-c was also pursued to extend this methodology.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/12/20 alle ore 12:53:43