A study of the efficiency and the problem of sulfonation of several condensing reagents and their mechanisms for the chemical synthesis of deoxyoligoribonucleotides
- 1 January 1980
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 8 (22) , 5445-5460
- https://doi.org/10.1093/nar/8.22.5445
Abstract
The efficiencies and problems of sulfonation of several condensing reagents for deoxyoligoribonucleotide synthesis have been studied. While 2,4,6-triisopropylbenzenesulfonyl chloride (TPSC1) gave very low yield and slow rate of coupling, the new 1:3 mixture of TPSC1 and tetrazole afforded excellent yield and extremely fast rate of reaction with the lowest rate of sulfonation. The difference and advantages of this mixture over triisopropylbenzenesulfonyl tetrazole (TPSTe) and mesitylenesulfonyl tetrazole (MSTe) are discussed. Mechanisms for the coupling reactions with these condensing reagents to account for the difference in their rates and yields of coupling are discussed.Keywords
This publication has 11 references indexed in Scilit:
- Synthesis of the human insulin gene. Part II. Further improvements in the modified phosphotriester method and the synthesis of seventeen deoxyribooligonucleotide fragments constituting human insulin chains B and mini-C DNANucleic Acids Research, 1979
- A synthetic tyrosine suppressor tRNA gene with an altered promoter sequence. Its cloning and relative expression in vivo.Journal of Biological Chemistry, 1979
- Chemical synthesis of versatile adaptors for molecular cloningBiochemical and Biophysical Research Communications, 1978
- A rapid and convenient synthesis of poly-thymidylic acid by the modified triester approachNucleic Acids Research, 1977
- Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides1Nucleic Acids Research, 1977
- Total synthesis of the structural gene for the precursor of a tyrosine suppressor transfer RNA from Escherichia coli. 1. General introduction.Journal of Biological Chemistry, 1976
- Use of arylsulfonyltriazoles for the synthesis of oligonucleotides by the triester approachJournal of the American Chemical Society, 1975
- Chemical synthesis and sequence studies of deoxyribooligonucleotides which constitute the duplex sequence of the lactose operator of Escherichia coli.Journal of Biological Chemistry, 1975
- Total Synthesis of the Gene for an Alanine Transfer Ribonucleic Acid from YeastNature, 1970
- Studies on Polynucleotides. LI.1 Syntheses of the 64 Possible Ribotrinucleotides Derived from the Four Major Ribomononucleotides2Journal of the American Chemical Society, 1966