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

✍ Scribed by Andrei P Guzaev; Muthiah Manoharan

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 104 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00911-4

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✦ Synopsis

The utility of the 2-(arylcarbamoyloxy)ethyl group for protection of internucleosidic 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 block. The mechanism of deprotection was con®rmed by deprotecting a model phosphate triester and synthetic dodecathymidylate.

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