The structure of merosinigrin confirmed

Abstract

An X-ray crystallographic study of merosinigrin confirmed the structure as 1,2-S,O-(1R,2S-1-cyano-2-methyl-1,2-ethanediyl)-1-thio-β-D-glucopyranose. The compound crystallizes in the space group P1 with a = 6.699(1), b = 9.347(1), c = 5.328(2) Å, α = 103.56(2), β = 109.14(3), γ = 86.71(1)°, and Z = 1. The structure was refined by full-matrix least-squares techniques to a final agreement value of R = 0.031. Merosinigrin provides what appears to be the first example of the anomeric effect in a thiane (1,4-oxathiane) system with cyano as the polar substituent.