2934. Desthiobiotin

Nomenclature

CAS number: 533-48-2
(4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoic acid; 5-methyl-2-oxo-4-imidazolidinecaproic acid; ε-(4-methyl-5-imidazolidone-2)-caproic acid; 4-methyl-5-(ω-carboxyamyl)imidazolidone-2.
C10H18N2O3; mol wt 214.26.
C 56.06%, H 8.47%, N 13.07%, O 22.40%.

Description and references

Prepd from biotin by hydrogenolysis of the sulfide linkage: du Vigneaud et al., J. Biol. Chem. 146, 475 (1942). Improved prepn procedure: Melville et al., Science 98, 497 (1943). Synthesis: Melville, J. Am. Chem. Soc. 66, 1422 (1944); Wood, du Vigneaud, ibid. 67, 210 (1945); Duschinsky, Dolan, ibid. 2079; Bourquin et al., Helv. Chim. Acta 28, 528 (1954).

Chemical structure

Properties

Long needles from water. mp 156-158°. [α]D21 +10.7° (c = 2). Sol in water.

Derivative

Methyl ester.
C11H20N2O3; mol wt 228.29.
C 57.87%, H 8.83%, N 12.27%, O 21.03%.

Properties

Crystals from methanol. Can be sublimed at 10-5 mm and 100°. mp 69-70°. [α]D28 +2.6° (c = 2 in chloroform). Readily sol in chloroform.