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

Stupi Brian P. | Zendy; Li Hong | Zendy; Wang Jinchun | Zendy; Wu Weidong | Zendy; Morris Sidney E. | Zendy; Litosh Vladislav A. | Zendy; Muniz Jesse | Zendy; Hersh Megan N. | Zendy; Metzker Michael L. | Zendy

Premium

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

Author(s) -

Stupi Brian P.,

Li Hong,

Wang Jinchun,

Wu Weidong,

Morris Sidney E.,

Litosh Vladislav A.,

Muniz Jesse,

Hersh Megan N.,

Metzker Michael L.

Publication year - 2012

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201106516

Subject(s) - chemistry , stereospecificity , hydroxymethyl , ring (chemistry) , stereochemistry , substitution (logic) , medicinal chemistry , organic chemistry , catalysis , computer science , programming language

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research