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...
Saved in:
Published in | Angewandte Chemie (International ed.) Vol. 51; no. 7; pp. 1724 - 1727 |
---|---|
Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
13.02.2012
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
Cover
Loading…
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 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 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 |