D-DESTHIOBIOTIN Chemical Properties

Melting point:

156-158°

alpha 

D21 +10.7° (c = 2)

Boiling point:

354.4°C (rough estimate)

Density 

1.1404 (rough estimate)

refractive index 

1.4550 (estimate)

storage temp. 

2-8°C

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

form 

Solid

pka

4.77±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1

InChIKey

AUTOLBMXDDTRRT-UHFFFAOYSA-N

SMILES

C1(=O)N[C@@H](C)[C@@H](CCCCCC(O)=O)N1

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

D-DESTHIOBIOTIN Usage And Synthesis

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.]

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