A novel phosphate protection for oligonucleotide synthesis: the 2-[(1-naphthyl)carbamoyloxy]ethyl (NCE) group

Authors
Guzaev, AP Manoharan, M
Citation
Ap. Guzaev et M. Manoharan, A novel phosphate protection for oligonucleotide synthesis: the 2-[(1-naphthyl)carbamoyloxy]ethyl (NCE) group, TETRAHEDR L, 41(30), 2000, pp. 5623-5626
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
30
Year of publication
2000
Pages
5623 - 5626
Database
ISI
SICI code
0040-4039(20000722)41:30<5623:ANPPFO>2.0.ZU;2-J
Abstract
The utility of the 2-(arylcarbamoyloxy)ethyl group for protection of intern ucleosidic phosphate linkages in oligonucleotide synthesis was studied. Of the three protecting groups tested, the 2-[(1 -naphthyl)carbamoyloxy]ethyl demonstrated high coupling yields, favorable deprotection kinetics and the highest hydrolytic stability of the thymidine phosphoramidite building bloc k. The mechanism of deprotection was confirmed by deprotecting a model phos phate triester and synthetic dodecathymidylate. (C) 2000 Elsevier Science L td. All rights reserved.