D-DESTHIOBIOTIN

Uses

D-Desthiobiotin is an analogue of Biotin (B389040) that binds less tightly to biotin-binding proteins such as Avidin and is easily displaced by Biotin.

Definition

ChEBI: (4R,5S)-dethiobiotin is the (4R,5S)-isomer of dethiobiotin. It is a conjugate acid of a (4R,5S)-dethiobiotin(1-). It is an enantiomer of a (4S,5R)-dethiobiotin.

Biological Activity

Desthiobiotin is a non-sulfur containing biotin derivative th at binds less strongly to biotin-binding proteins and is easily dislocated by biotin.

Purification Methods

Dissolve desthiobiotin in 0.5% Na2CO3, filter, acidify with HCl to Congo Red, concentrate to a small volume (2-3 mL) to give fine needles, filter it off and recrystallise it twice from H2O, m 157-158o. It also crystallises from 95% EtOH. The methyl ester crystallises from MeOH and sublimes at 100o/high vacuum, m 69-70o, [] D +2.6o (c 2, CHCl3). [Melville et al. Science 98 497 1943, J Am Chem Soc 66 1422 1944, Beilstein 25 III/IV 1543.]