Synthesis and characterization of oligonucleotides containing 2'-S,3'-O- cyclic phosphorothiolate termini

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5700-5704

  Hamm, Michelle L ^a   Piccirilli, Joseph A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PHOSPHOROTHIOIC ACID DERIVATIVE; RIBOZYME; URIDINE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; ENZYME ACTIVITY; ENZYME SPECIFICITY; MOLECULAR INTERACTION; NUCLEIC ACID BASE SUBSTITUTION; NUCLEOTIDE METABOLISM; PHOSPHORYLATION;

EID: 0033597913     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9903508     Document Type: Article

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20. 12
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22. 14 The observation that one of the acid cleavage products of 8b (Figure 2, lane 7) comigrates with the silver cleavage product (lane 5) suggests that acidic conditions also cleave the 2′-S-P bond of the 2′-S,3′-O-cyclic phosphorothiolate. The reasons for the different regioselectivities resulting from base and acid cleavage are discussed in refs 12 and 14 and references therein.