139936-57-5

Usage

InChI:InChI=1/C10H18N2O3S/c13-9(14)5-3-1-2-4-7-8(6-16)12-10(15)11-7/h7-8,16H,1-6H2,(H,13,14)(H2,11,12,15)/t7-,8+/m1/s1

Upstream product

• 39828-42-7 4-(5-ethoxycarbonyl-1-oxovaleryl)imidazolin-2-one 
• 39215-48-0 ethyl 9-oxo-7,8-didehydrodethiobiotin 
• 139936-50-8 (+/-)-9-mercaptothiobiotin dimer 
• 39828-43-8 6-hydroxy-6-(2-oxo-2,3-dihydro-1H-imidazol-4-yl)-hexanoic acid ethyl ester 
• 139936-55-3 6-[(4R,5R)-1,3-Diacetyl-2-oxo-5-(toluene-4-sulfonyloxymethyl)-imidazolidin-4-yl]-hexanoic acid ethyl ester 
• 139936-56-4 ethyl (+/-)-N,N'-diacetyl-9-thioacetyldethiobiotin 
• 139936-52-0 6-(1,3-Diacetyl-5-formyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-hexanoic acid ethyl ester 
• 139936-53-1 ethyl (+/-)-N,N'-diacetyl-9-hydroxydethiobiotin 
• 1071-71-2 ethyl 6-chloro-6-oxohexanoate 

Relevant academic research and scientific papers

Biotin biosynthesis: Synthesis and biological evaluation of the putative intermediate thiols

Previous results led to the conclusion that the last step of biotin biosynthesis, the sulfur insertion into dethiobiotin, should involve a thiol as intermediate. The three possible thiols have been synthesized and their biological activity was evaluated: the primary thiol 10 labeled with [35S] or [34S] or with deuterium was transformed into biotin by resting cells of Bacillus sphaericus without loss of the label. Hence, it is a possible intermediate. Interestingly, growing cells transformed [35S]- or 5-[2H2]-labeled 10 into biotin with loss of the labels. 10 and one of the secondary thiols 5B also promote the growth of Escherichia coli C124, a biotin auxotroph, but again they lose their sulfur during their conversion to biotin. The growing cells experiments reveal a complex pathway which remains to be elucidated.

Synthesis and Biological Activity of 9-Mercaptodethiobiotin - a Putative Biotin Precursor in Escherichia coli

A total synthesis of (+/-)-9-mercaptodethiobiotin 3 via the aldehyde 9 is described.Compound (+/-)-3 does not function as a biotin replacement factor for an E. coli mutant (SA291) lacking the entire biotin synthesis operon (bioABFCD-) but supports growth of an E. coli bioA mutant.Compound (+/-)-3 also supports growth of transformed cells of SA291 carrying a plasmid encoding the E. coli biotin synthase (bioB) gene indicating that the compound may be able to substitute for dethiobiotin 2 as a substrate for biotin synthase.