Synthesis of enantiopure alpha-deuteriated Boc-L-amino acids
| dc.contributor.author | Elemes, Y. | en |
| dc.contributor.author | Ragnarsson, U. | en |
| dc.date.accessioned | 2015-11-24T16:49:16Z | |
| dc.date.available | 2015-11-24T16:49:16Z | |
| dc.identifier.issn | 0300-922X | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/9456 | |
| dc.rights | Default Licence | - |
| dc.subject | asymmetric-synthesis | en |
| dc.subject | derivatives | en |
| dc.subject | enantiomers | en |
| dc.subject | separation | en |
| dc.subject | alkylation | en |
| dc.subject | chirality | en |
| dc.subject | complexes | en |
| dc.subject | peptides | en |
| dc.subject | phase | en |
| dc.subject | c-13 | en |
| dc.title | Synthesis of enantiopure alpha-deuteriated Boc-L-amino acids | en |
| heal.abstract | An alternative scheme for the synthesis of enantiopure alpha-deuteriated amino acids from a common intermediate is presented. Methyl bis(methylsulfanyl)methylene [2,2-H-2(2)] glycinate was prepared in a mixture of MeOD and D2O with a catalytic amount of Na2CO3 and attached to (2R)-bornane-10,2-sultam. Alkylation of the corresponding enolate provided intermediates which after careful purification were first deprotected on nitrogen and then cleaved from the auxiliary to give deuteriated alpha-amino acids of very high purity (> 99% ee and > 98% D). These were directly converted into the corresponding Boc-L-[2-H-2]-Ala, -Leu,-Phe and -(O-Bzl)Tyr derivatives, suitable for application in peptide synthesis, Boc-[2,2-H-2(2)]Gly was also prepared. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | Doi 10.1039/P19960000537 | - |
| heal.identifier.secondary | <Go to ISI>://A1996UC26300010 | - |
| heal.identifier.secondary | http://pubs.rsc.org/en/Content/ArticleLanding/1996/P1/p19960000537 | - |
| heal.journalName | Journal of the Chemical Society-Perkin Transactions 1 | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 1996 | - |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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