| dc.contributor.author |
Constantinou-Kokotou, V |
en |
| dc.contributor.author |
Magrioti, V |
en |
| dc.contributor.author |
Markidis, T |
en |
| dc.contributor.author |
Kokotos, G |
en |
| dc.date.accessioned |
2014-06-06T06:44:47Z |
|
| dc.date.available |
2014-06-06T06:44:47Z |
|
| dc.date.issued |
2001 |
en |
| dc.identifier.issn |
1397-002X |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/2063 |
|
| dc.subject |
2-amino-oleic acid |
en |
| dc.subject |
alpha-amino acids |
en |
| dc.subject |
amino aldehydes |
en |
| dc.subject |
non-natural amino acids |
en |
| dc.subject |
Wittig reaction |
en |
| dc.subject.classification |
Biochemical Research Methods |
en |
| dc.subject.classification |
Biochemistry & Molecular Biology |
en |
| dc.subject.other |
ASYMMETRIC-SYNTHESIS |
en |
| dc.subject.other |
GLUTAMIC-ACID |
en |
| dc.subject.other |
DERIVATIVES |
en |
| dc.subject.other |
PEPTIDOMIMETICS |
en |
| dc.subject.other |
INHIBITORS |
en |
| dc.subject.other |
ALCOHOLS |
en |
| dc.title |
Synthesis of enantiopure non-natural alpha-amino acids using tert-butyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate as key-intermediate: the first synthesis of (S)-2-amino-oleic acid |
en |
| heal.type |
journalArticle |
en |
| heal.language |
English |
en |
| heal.publicationDate |
2001 |
en |
| heal.abstract |
A general method for the synthesis of enantiopure non-natural alpha -amino acids is described. The key intermediate tert-butyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate was obtained from L-glutamic acid after suitable protection and selective reduction of the gamma -methyl ester group by DIBALH. Wittig reaction of this chiral aldehyde with various ylides led to a variety of delta,epsilon -unsaturated alpha -amino acids. This methodology was applied to the synthesis of (S)-2-amino-oleic acid. |
en |
| heal.publisher |
MUNKSGAARD INT PUBL LTD |
en |
| heal.journalName |
JOURNAL OF PEPTIDE RESEARCH |
en |
| dc.identifier.issue |
4 |
en |
| dc.identifier.volume |
58 |
en |
| dc.identifier.isi |
ISI:000171695700006 |
en |
| dc.identifier.spage |
325 |
en |
| dc.identifier.epage |
331 |
en |