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Cover Picture: Major Groove Derivatization of an Unnatural Base Pair (ChemBioChem 14/2009)
Author(s) -
Seo Young Jun,
Romesberg Floyd E.
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200990060
Subject(s) - nucleobase , steric effects , base pair , chemistry , dna , stereochemistry , derivatization , combinatorial chemistry , biochemistry , organic chemistry , high performance liquid chromatography
The cover picture highlights structure–activity relationship studies of d MMO2 –d 5SICS , one of the most promising unnatural base pairs. Because the ortho substituents of the constituent nucleobase analogues are required for continued primer extension after synthesis of the unnatural base pair, these studies, described on p. 2394 ff. by F. E. Romesberg and Y. J. Seo, focused on meta and/or para substituents of the d MMO2 scaffold. These derivatives are expected to be positioned in the developing major groove, and the results suggest that they have both steric and electrostatic effects on replication. The results also reveal several approaches by which the unnatural base pair might be used to site‐specifically label DNA with a functionality of interest. Similar modifications of the d 5SICS nucleobase analogue should allow for the site‐specific labeling of DNA with two different functionalities, and the previously demonstrated efficient transcription of the unnatural base pair suggests that derivatives might similarly enable site‐specific labeling of RNA.