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Stereoselective Synthesis of (5′ S )‐5′‐ C ‐(5‐Bromo‐2‐penten‐1‐yl)‐2′‐deoxyribofuranosyl Thymine, a New Convertible Nucleoside
Author(s) -
Banuls Valérie,
Escudier JeanMarc,
Zedde Chantal,
Claparols Catherine,
Donnadieu Bruno,
Plaisancié Henri
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200112)2001:24<4693::aid-ejoc4693>3.0.co;2-j
Subject(s) - chemistry , thymine , stereochemistry , stereoselectivity , substituent , nucleoside , duplex (building) , phosphoramidite , dna , organic chemistry , oligonucleotide , biochemistry , catalysis
A stereoselective synthesis of (5′ S )‐5′‐ C ‐(5‐bromo‐2‐penten‐1‐yl)‐2′‐deoxyribofuranosyl thymine phosphoramidite is described; the absolute stereochemistry of the compound has been determined by X‐ray diffraction analysis. This convertible nucleoside has been incorporated into oligodeoxynucleotides (ODNs) and proved to be suitable for post‐synthesis conjugation on solid support. When a diamine is tethered, there is no alteration in the pairing properties of the ODNs. Molecular modelling indicates that the substituent is inserted into the minor groove of the duplex.