Synthesis and Characterization of Imidazoyl-Linked Synthons and 3′-Conjugated Thymidine Derivatives

Nikolai N. Polushin; Ban chin Chen; Lawrence W. Anderson; Jack S. Cohen

doi:10.1021/jo00069a022

Synthesis and Characterization of Imidazoyl-Linked Synthons and 3′-Conjugated Thymidine Derivatives

Nikolai N. Polushin, Ban chin Chen, Lawrence W. Anderson, Jack S. Cohen

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

19 Scopus citations

Abstract

The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3′-conjugated thymidine derivatives using 5′-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

Original language	English
Pages (from-to)	4606-4613
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	58
Issue number	17
DOIs	https://doi.org/10.1021/jo00069a022
State	Published - 1 Jan 1993
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00069a022

Cite this

@article{e7653bf9eb9b47c8806ef553e59cec64,

title = "Synthesis and Characterization of Imidazoyl-Linked Synthons and 3′-Conjugated Thymidine Derivatives",

abstract = "The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3′-conjugated thymidine derivatives using 5′-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.",

author = "Polushin, {Nikolai N.} and Chen, {Ban chin} and Anderson, {Lawrence W.} and Cohen, {Jack S.}",

year = "1993",

month = jan,

day = "1",

doi = "10.1021/jo00069a022",

language = "English",

volume = "58",

pages = "4606--4613",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Synthesis and Characterization of Imidazoyl-Linked Synthons and 3′-Conjugated Thymidine Derivatives

AU - Polushin, Nikolai N.

AU - Chen, Ban chin

AU - Anderson, Lawrence W.

AU - Cohen, Jack S.

PY - 1993/1/1

Y1 - 1993/1/1

N2 - The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3′-conjugated thymidine derivatives using 5′-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

AB - The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3′-conjugated thymidine derivatives using 5′-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

UR - http://www.scopus.com/inward/record.url?scp=0027527842&partnerID=8YFLogxK

U2 - 10.1021/jo00069a022

DO - 10.1021/jo00069a022

M3 - Article

AN - SCOPUS:0027527842

SN - 0022-3263

VL - 58

SP - 4606

EP - 4613

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Synthesis and Characterization of Imidazoyl-Linked Synthons and 3′-Conjugated Thymidine Derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this