Synthesis of sulfamide linked dinucleotide analogues

Jason Micklefield; Kevin J. Fettes

doi:10.1016/S0040-4039(97)01179-9

Synthesis of sulfamide linked dinucleotide analogues

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Abstract

Novel sulfamide [-NHSO2NH-] linked dinucleotide analogues d(TnsnT) and d(TnsnA) have been synthesised from 3'- and 5'-amino nucleosides. Treatment of these amino nucleosides with catechol sulfate results in the formation of 2-hydroxyphenyl sulfamate esters which couple smoothly in good yields with either 5' or 3'-amines of similar nucleosides. NMR studies showed that the 3'- sulfamide group results in a preferential C3'-endo (Northern) sugar conformation.

Original language	English
Pages (from-to)	5387-5390
Number of pages	3
Journal	Tetrahedron Letters
Volume	38
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(97)01179-9
Publication status	Published - 28 Jul 1997

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title = "Synthesis of sulfamide linked dinucleotide analogues",

abstract = "Novel sulfamide [-NHSO2NH-] linked dinucleotide analogues d(TnsnT) and d(TnsnA) have been synthesised from 3'- and 5'-amino nucleosides. Treatment of these amino nucleosides with catechol sulfate results in the formation of 2-hydroxyphenyl sulfamate esters which couple smoothly in good yields with either 5' or 3'-amines of similar nucleosides. NMR studies showed that the 3'- sulfamide group results in a preferential C3'-endo (Northern) sugar conformation.",

author = "Jason Micklefield and Fettes, \{Kevin J.\}",

year = "1997",

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doi = "10.1016/S0040-4039(97)01179-9",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Synthesis of sulfamide linked dinucleotide analogues

AU - Micklefield, Jason

AU - Fettes, Kevin J.

PY - 1997/7/28

Y1 - 1997/7/28

N2 - Novel sulfamide [-NHSO2NH-] linked dinucleotide analogues d(TnsnT) and d(TnsnA) have been synthesised from 3'- and 5'-amino nucleosides. Treatment of these amino nucleosides with catechol sulfate results in the formation of 2-hydroxyphenyl sulfamate esters which couple smoothly in good yields with either 5' or 3'-amines of similar nucleosides. NMR studies showed that the 3'- sulfamide group results in a preferential C3'-endo (Northern) sugar conformation.

AB - Novel sulfamide [-NHSO2NH-] linked dinucleotide analogues d(TnsnT) and d(TnsnA) have been synthesised from 3'- and 5'-amino nucleosides. Treatment of these amino nucleosides with catechol sulfate results in the formation of 2-hydroxyphenyl sulfamate esters which couple smoothly in good yields with either 5' or 3'-amines of similar nucleosides. NMR studies showed that the 3'- sulfamide group results in a preferential C3'-endo (Northern) sugar conformation.

UR - https://www.scopus.com/pages/publications/0030836519

U2 - 10.1016/S0040-4039(97)01179-9

DO - 10.1016/S0040-4039(97)01179-9

M3 - Article

SN - 1873-3581

VL - 38

SP - 5387

EP - 5390

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Synthesis of sulfamide linked dinucleotide analogues

Abstract

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