Stereochemistry of Benzylic Carbon Substitution Coupled with Ring Modification of 2-Nitrobenzyl Groups as Key Determinants for Fast-Cleaving Reversible Terminators

A complete set of 2‐nitrobenzyl‐modified reversible terminators have been developed, which upon exposure to UV light generate natural hydroxymethyl nucleotides (see scheme). The combination of a stereospecific (S)‐tert‐butyl group (R) at the benzylic carbon and a 5‐OMe group (R′) on the 2‐nitrobenzy...

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Published inAngewandte Chemie (International ed.) Vol. 51; no. 7; pp. 1724 - 1727
Main Authors Stupi, Brian P., Li, Hong, Wang, Jinchun, Wu, Weidong, Morris, Sidney E., Litosh, Vladislav A., Muniz, Jesse, Hersh, Megan N., Metzker, Michael L.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 13.02.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Benzyl Compounds - chemistry
Carbon
Cleavage
cleavage reactions
Communications
Determinants
Exposure
Joining
Molecular Structure
Nitrobenzenes - chemistry
Nucleotides
Nucleotides - chemistry
Photochemical
photochemistry
reversible terminators
Rings (mathematics)
Stereochemistry
Stereoisomerism
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Summary:A complete set of 2‐nitrobenzyl‐modified reversible terminators have been developed, which upon exposure to UV light generate natural hydroxymethyl nucleotides (see scheme). The combination of a stereospecific (S)‐tert‐butyl group (R) at the benzylic carbon and a 5‐OMe group (R′) on the 2‐nitrobenzyl ring substantially increase the rate of photochemical cleavage. For 7‐deaza‐7‐hydroxymethyl‐2′‐deoxyguanosine, these modifications led to a rate increase of more than one order of magnitude.
Bibliography:istex:30EC1CB1CB8F7D3A8DE2A82EA9EE17A16943116C
Funded Access
National Institutes of Health
ark:/67375/WNG-DP9JPFDJ-J
This work was supported in part by the National Institutes of Health (R01 HG003573). We thank Sherry Metzker from LaserGen for critical reading of the manuscript.
ArticleID:ANIE201106516
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Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/anie.201106516.
Re-use of this article is permitted in accordance with the Terms and Conditions set out at http://angewandte.org/open.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201106516