Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine

Michael P. McCrane; Emily E. Weinert; Ying Lin; Eugene P. Mazzola; Yiu Fai Lam; Peter F. Scholl; Steven E. Rokita

doi:10.1021/ol200071p

Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine

Michael P. McCrane, Emily E. Weinert, Ying Lin, Eugene P. Mazzola, Yiu Fai Lam, Peter F. Scholl, Steven E. Rokita

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

15 Scopus citations

Abstract

Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI) provides an effective trap for quenching adducts formed reversibly between dC and an ortho-quinone methide (QM) under physiological conditions. A model adduct generated by 4-methyl-o-QM and 2′-deoxycytidine is rapidly converted by intramolecular cyclization and loss of aromaticity to a characteristic product for quantifying QM alkylation. However, BTI induces a surprising rearrangement driven by overoxidation of a derivative lacking an alkyl substituent at the 4-position of the QM.(Figure Presented)

Original language	English (US)
Pages (from-to)	1186-1189
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/ol200071p
State	Published - Mar 4 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine",

abstract = "Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI) provides an effective trap for quenching adducts formed reversibly between dC and an ortho-quinone methide (QM) under physiological conditions. A model adduct generated by 4-methyl-o-QM and 2′-deoxycytidine is rapidly converted by intramolecular cyclization and loss of aromaticity to a characteristic product for quantifying QM alkylation. However, BTI induces a surprising rearrangement driven by overoxidation of a derivative lacking an alkyl substituent at the 4-position of the QM.(Figure Presented)",

author = "McCrane, \{Michael P.\} and Weinert, \{Emily E.\} and Ying Lin and Mazzola, \{Eugene P.\} and Lam, \{Yiu Fai\} and Scholl, \{Peter F.\} and Rokita, \{Steven E.\}",

year = "2011",

month = mar,

day = "4",

doi = "10.1021/ol200071p",

language = "English (US)",

volume = "13",

pages = "1186--1189",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine

AU - McCrane, Michael P.

AU - Weinert, Emily E.

AU - Lin, Ying

AU - Mazzola, Eugene P.

AU - Lam, Yiu Fai

AU - Scholl, Peter F.

AU - Rokita, Steven E.

PY - 2011/3/4

Y1 - 2011/3/4

N2 - Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI) provides an effective trap for quenching adducts formed reversibly between dC and an ortho-quinone methide (QM) under physiological conditions. A model adduct generated by 4-methyl-o-QM and 2′-deoxycytidine is rapidly converted by intramolecular cyclization and loss of aromaticity to a characteristic product for quantifying QM alkylation. However, BTI induces a surprising rearrangement driven by overoxidation of a derivative lacking an alkyl substituent at the 4-position of the QM.(Figure Presented)

AB - Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI) provides an effective trap for quenching adducts formed reversibly between dC and an ortho-quinone methide (QM) under physiological conditions. A model adduct generated by 4-methyl-o-QM and 2′-deoxycytidine is rapidly converted by intramolecular cyclization and loss of aromaticity to a characteristic product for quantifying QM alkylation. However, BTI induces a surprising rearrangement driven by overoxidation of a derivative lacking an alkyl substituent at the 4-position of the QM.(Figure Presented)

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U2 - 10.1021/ol200071p

DO - 10.1021/ol200071p

M3 - Article

C2 - 21306149

AN - SCOPUS:79952136455

SN - 1523-7060

VL - 13

SP - 1186

EP - 1189

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine

Abstract

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