Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues - a new protection scheme | Zendy

Robert G. Kuimelis | Zendy; Krishnan P. Nambiar | Zendy

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Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues - a new protection scheme

Author(s) -

Robert G. Kuimelis,

Krishnan P. Nambiar

Publication year - 1994

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/22.8.1429

Subject(s) - biology , reagent , acylation , base (topology) , combinatorial chemistry , aqueous solution , substrate (aquarium) , oligonucleotide , dna , stereochemistry , biochemistry , mathematics , chemistry , catalysis , organic chemistry , mathematical analysis , ecology

A method is described for the incorporation of 2'-deoxy-2-thiouridine (dS2U) and 2'-deoxy-2-thiothymidine (dS2T) into oligodeoxynucleotides at predetermined positions. This requires N3 or O4-acylation of dS2U and dS2T with toluoyl chloride. These base-protected thiopyrimidines are completely stable toward the aqueous iodine oxidation reagent used in the phosphoramidite DNA synthesis method. The toluoyl protecting group is removed during the standard post-synthetic ammonia treatment. This novel protection strategy allows dS2U and dS2T to be efficiently incorporated into oligodeoxynucleotides at predetermined sites without the usual problem of desulfurization and decomposition. Several 14-mers containing the Eco-RI recognition site (dGGCGGAAXXCCGCC and dGGCGGAAXXCGCGG, where X represents dT, dS2U or dS2T) have been synthesized and characterized by base composition, thermal denaturation, CD spectroscopy and endonuclease substrate activity.

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