Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides

Bashar Mullah; Alex Andrus; Hong Zhao; Roger A. Jones

doi:10.1016/0040-4039(95)00816-U

Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides

Bashar Mullah, Alex Andrus, Hong Zhao, Roger A. Jones

School of Arts and Sciences, Chemistry & Chemical Biology

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Reaction of the N-dimethylformamidine (dmf) derivatives of 2′-deoxyguanosine, guanosine, and 2′-deoxyadenosine with iodine and aqueous ammonia gives the corresponding N-cyano nucleosides. This reaction occurs in oligonucleotides under conditions where iodine is reatined on the solid support, or in the synthesis column, prior to cleavage with aqueous ammonia. This base modification can be eliminated with lower iodine concentration in the oxidation reagent.

Original language	English (US)
Pages (from-to)	4373-4376
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	25
DOIs	https://doi.org/10.1016/0040-4039(95)00816-U
State	Published - Jun 19 1995

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides",

abstract = "Reaction of the N-dimethylformamidine (dmf) derivatives of 2′-deoxyguanosine, guanosine, and 2′-deoxyadenosine with iodine and aqueous ammonia gives the corresponding N-cyano nucleosides. This reaction occurs in oligonucleotides under conditions where iodine is reatined on the solid support, or in the synthesis column, prior to cleavage with aqueous ammonia. This base modification can be eliminated with lower iodine concentration in the oxidation reagent.",

author = "Bashar Mullah and Alex Andrus and Hong Zhao and Jones, {Roger A.}",

note = "Funding Information: AcknowledgmenTthsi:s work was supported by a grant from the National Institutes of Health (GM 31483) to R. A. J. We thank Christie McCollum for technical assistance.",

year = "1995",

month = jun,

day = "19",

doi = "10.1016/0040-4039(95)00816-U",

language = "English (US)",

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pages = "4373--4376",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides

AU - Mullah, Bashar

AU - Andrus, Alex

AU - Zhao, Hong

AU - Jones, Roger A.

N1 - Funding Information: AcknowledgmenTthsi:s work was supported by a grant from the National Institutes of Health (GM 31483) to R. A. J. We thank Christie McCollum for technical assistance.

PY - 1995/6/19

Y1 - 1995/6/19

N2 - Reaction of the N-dimethylformamidine (dmf) derivatives of 2′-deoxyguanosine, guanosine, and 2′-deoxyadenosine with iodine and aqueous ammonia gives the corresponding N-cyano nucleosides. This reaction occurs in oligonucleotides under conditions where iodine is reatined on the solid support, or in the synthesis column, prior to cleavage with aqueous ammonia. This base modification can be eliminated with lower iodine concentration in the oxidation reagent.

AB - Reaction of the N-dimethylformamidine (dmf) derivatives of 2′-deoxyguanosine, guanosine, and 2′-deoxyadenosine with iodine and aqueous ammonia gives the corresponding N-cyano nucleosides. This reaction occurs in oligonucleotides under conditions where iodine is reatined on the solid support, or in the synthesis column, prior to cleavage with aqueous ammonia. This base modification can be eliminated with lower iodine concentration in the oxidation reagent.

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U2 - 10.1016/0040-4039(95)00816-U

DO - 10.1016/0040-4039(95)00816-U

M3 - Article

AN - SCOPUS:0029001005

SN - 0040-4039

VL - 36

SP - 4373

EP - 4376

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides

Abstract

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