1969-54-6Relevant academic research and scientific papers
2-MERCAPTOBENZOTHIAZOLE-AN IMPROVED REAGENT FOR THE REMOVAL OF METHYL PHOSPHATE PROTECTING GROUPS FROM OLIGODEOXYNUCLEOTIDE PHOSPHOTRIESTERS.
Andrus, Alex,Beaucage, Serge L.
, p. 5479 - 5482 (1988)
An equimolar (1.5 M) solution of 2-mercaptobenzothiazole and N,N-diisopropylethylamine in 1-methyl-2-pyrrolidinone efficiently removed the methyl phosphate protecting groups from deoxynucleotide phosphotriesters and yielded synthetic oligomers of high genetic integrity.This odorless reagent can therefore substitute for hazardous thiophenol usually used for this purpose.
The 4-oxopentyl group as a labile phosphate/thiophosphate protecting group for synthetic oligodeoxyribonucleotides
Wilk, Andrzej,Chmielewski, Marcin K.,Grajkowski, Andrzej,Phillips, Lawrence R.,Beaucage, Serge L.
, p. 5635 - 5639 (2001)
An efficient and economical method for the solid-phase synthesis of oligodeoxyribonucleotides and their phosphorothioate analogues is described. The method entails the use of the 4-oxopentyl group for phosphate/thiophosphate protection. Post-synthesis removal of the protecting group is easily and rapidly achieved under mild conditions at ambient temperature using either pressurized gaseous amines or concentrated ammonium hydroxide.
Ester exchange reaction of oxyphosphorane with thymidine
Chen,Zhao
, p. 3691 - 3694 (1995)
Ester exchange reaction of oxyphosphorane (1) with thymidine (2) afforded diastereomeric spirooxyphosphoranes 3 under mild conditions in good yield. After hydrolysis, thymidine phosphates monomers (5,6) and dimer (7) were obtained.
Oxidation and reduction of the 5-(2-Deoxyuridinyl)methyl radical
Lin, Gengjie,Li, Lei
, p. 5594 - 5598 (2013/06/27)
Sleeping beauty: The 5-(2-Deoxyuridinyl)methyl radical 1 is a key intermediate in the thymine oxidative reaction mediated by reactive oxygen species. Evidence is presented that 1 is prone to both oxidation and reduction reactions at the absence of O2. These results question the current paradigm and suggest that the redox chemistry of 1, which has been largely overlooked in the past, may play a major role in determining the fate of 1. Copyright
OLIGONUCLEOTIDES AND NUCLEOTIDOPEPTIDES. XLII. EFFICACY OF THE INTRAMOLECULAR INFLUENCE OF THE CARBOXY GROUPS OF AMINO ACIDS IN NUCLEOTIDYL-(P-->N)-AMINO ACIDS (PEPTIDES) AS A FUNCTION OF THEIR POSITIONS
Yuodka, B. A.,Lioranchaite, L. E.,Baltenas, V. R.
, p. 703 - 708 (2007/10/02)
It has been established that remote carboxy groups in nucleotidyl-(5'-->N)-β-alanine and -alanylalanine do not affect the mechanism of the cleavage of the phosphoramide center.The situation is different in the case of nucleotidyl-(5'-->Nε)-lysine.It has been shown that in the 3'-phenylalanine derivative of dTMP, the influence of the α-carboxy group of the amino acid is only half as great as in the 5'-analog.The α-carboxy groups of the amino acids in oligonucleotidyl-(Pin-->N)-amino acids also weaken the mechanism of the cleavage of the phosphoramide centers.
