[54230-59-0]  · C12H14N2O2S  · Mesitylsulfonylimidazole  · (MW 250.35)

(condensing agent for oligonucleotide synthesis1)

Alternate Name: MSI.

Physical Data: mp 97-99 °C.

Form Supplied in: solid; widely available from commercial sources.

Preparative Method: readily prepared by the reaction of equimolar ratios of Mesitylenesulfonyl Chloride, Imidazole, and Triethylamine in a chloroform solution (eq 1).

Oligonucleotide Synthesis.

MSI1 was reported as a condensing agent for oligonucleotide synthesis by activation of phosphomonoester groups of nucleotides (eq 2).2 Very few reports of the use of this reagent have appeared in literature. Reactions with MSI are reported to be very slow, but acid-sensitive functional groups are unaffected by these reaction conditions.3

1. Berlin, T. A.; Chakhmakhcheva, O. G.; Efimov, V. A.; Kolosov, M. N.; Korobko, V. G. TL 1973, 1353.
2. For a review of DNA synthesis and condensing agents used, see: Narang, S. A. T 1983, 39, 3.
3. Jones, S. S.; Rayner, B.; Reese, C. B.; Ubasawa, A.; Ubasawa, M. T 1980, 36, 3075.

Valerie Vaillancourt & Michele M. Cudahy

The Upjohn Co., Kalamazoo, MI, USA

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