Title: Biocytin
CAS Registry Number: 576-19-2
CAS Name: N6-[5-(Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]-L-lysine
Additional Names: e-N-biotinyl-L-lysine; biotin complex of yeast
Molecular Formula: C16H28N4O4S
Molecular Weight: 372.48
Percent Composition: C 51.59%, H 7.58%, N 15.04%, O 17.18%, S 8.61%
Literature References: A naturally occurring complex of biotin. Contains 65.6% biotin. Isoln: Wright et al., J. Am. Chem. Soc. 72, 1048 (1950); 74, 1996 (1952). Structure: Peck et al., ibid. 72, 1048 (1950); 74, 1999 (1952). Synthesis: Wolf et al., ibid. 74, 2002 (1952); Weijlard et al., ibid. 76, 2505 (1954); Wolf, Folkers, US 2710298 (1955 to Merck & Co.). Purification: McCormick, Föry, Methods Enzymol. 18 (pt A), 413 (1970). Review: A. F. Wagner, K. Folkers, Vitamins and Coenzymes (Wiley, New York, 1964) pp 138-159.
Properties: Crystals, mp 241-243°. Upon rapid crystn from dil methanol or dil acetone, mp 228-230° (dec); upon slow crystn sinters at 227°. mp 245-252° (dec, microblock). Crystals from water, mp 228.5°. [a]D25 +53° (c = 1.05 in 0.1N NaOH). Infrared absorption spectrum: J. Am. Chem. Soc. 74, 2001 (1952). Freely sol in water, glacial acetic acid. Less sol in alc. Practically insol in acetone and most other organic solvents. When subjected to strong acid hydrolysis (at least 3N at 120° for one hour) biocytin yields biotin and L-lysine. Forms a crystalline hydrochloride. Biocytin is characterized microbiologically by its availability as a source of biotin to Lactobacillus casei, L. delbrückii LD 5, L. acidophilus, Streptococcus fecalis R, Neurospora crassa, and Saccharomyces carlsbergensis and by its unavailability as a source of biotin to Lactobacillus arabinosus, L. pentosus, and Leuconostoc mesenteroides P-60.
Melting point: mp 241-243°; mp 228-230° (dec); mp 245-252° (dec, microblock); mp 228.5°
Optical Rotation: [a]D25 +53° (c = 1.05 in 0.1N NaOH) |