Document Detail

First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids.
MedLine Citation:
PMID:  22180179     Owner:  NLM     Status:  Publisher    
The distinctive nucleus of kainoid amino acids, (2S,3R)-(+)-2-carboxypyrrolidine-3-acetic acid 6, was synthesized by a chemoenzymatic process, exploiting the diastereomeric cis/trans methyl pyroglutamate derivatives 10a-c/11a-c as key intermediates. These mixtures, when subjected to a kinetic resolution mediated by α-chymotrypsin, reacted diastereo-, regio-, and enantioselectively to give the trans derivatives (+)-10a-c possessing the correct (2S,3R) configuration. Subsequently, the desired product (2S,3R)-(+)-6 could be obtained after well-established transformations. Chirality, 2011. © 2011 Wiley Periodicals, Inc.
Fulvia Felluga; Cristina Forzato; Patrizia Nitti; Giuliana Pitacco; Franco Ghelfi; Ennio Valentin
Related Documents :
21902189 - Vo(2+) complexation by bioligands showing keto-enol tautomerism: a potentiometric, spec...
19416649 - Fish protein hydrolysate elevates plasma bile acids and reduces visceral adipose tissue...
18083729 - Selective mobilization of fatty acids from adipose tissue in migratory birds.
3776639 - Multielemental characterization of human lung tissues by icp-aes.
2591189 - Adipose tissue in the mammalian heart and pericardium: structure, foetal development an...
8381379 - Influence of the pituitary on lipolysis and lipogenesis in fetal pig adipose tissue.
21324969 - Amino acid export in plants: a missing link in nitrogen cycling.
21055619 - Synthesis of novel 68ga-labeled amino acid derivatives for positron emission tomography...
7688799 - Excitatory amino acids depress synaptic currents in neonate rat sympathetic preganglion...
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-19
Journal Detail:
Title:  Chirality     Volume:  -     ISSN:  1520-636X     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-12-19     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Wiley Periodicals, Inc.
Department of Chemical and Pharmaceutical Sciences, University of Trieste, Trieste, Italy.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  NRAS mutation status is an independent prognostic factor in metastatic melanoma.
Next Document:  Absence of biallelic TCR? deletion predicts induction failure and poorer outcomes in childhood T-cel...