30868-27-0

Basic information

• Product Name: Hexahydro-α-methyl-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid
• Synonyms: Hexahydro-α-methyl-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid;α-Methylbiotin
• CAS NO: 30868-27-0
• Molecular Formula: C₁₁H₁₈N₂O₃S
• Molecular Weight: 258.33722
• Mol File: 30868-27-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 562.2°C at 760 mmHg
• Flash Point: 293.8°C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 4.09E-14mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: Hexahydro-α-methyl-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Hexahydro-α-methyl-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid(30868-27-0)
• EPA Substance Registry System: Hexahydro-α-methyl-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid(30868-27-0)

Safety Data

• Hazardous Substances Data: 30868-27-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H18N2O3S/c1-6(10(14)15)3-2-4-8-9-7(5-17-8)12-11(16)13-9/h6-9H,2-5H2,1H3,(H,14,15)(H2,12,13,16)

Upstream product

• 415725-34-7 (9RS)-methylbiotin methyl ester 
• 58-85-5 biotin 
• 608-16-2 biotin methyl ester 
• 35143-20-5 2-acetyl-2-methyl-5-(2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid ethyl ester 

Downstream Products

• 415725-36-9 (9S)-methylbiotin N-[(S)-α-methylbenzyl]amide 
• 415725-37-0 (9R)-methylbiotin N-[(S)-α-methylbenzyl]amide 
• 415725-35-8 (9S)-methylbiotin 
• 415725-35-8 (9R)-methylbiotin 

Relevant articles and documents

Theoretical and experimental studies of biotin analogues that bind almost as tightly to streptavidin as biotin

We have used a newly developed qualitative computational approach, PROFEC (Pictorial Representation of Free Energy Changes), to visualize the areas of the ligand biotin where modifications of its structure might lead to tighter binding to the protein streptavidin. The PROFEC analysis, which includes protein flexibility and ligand sotvation/desolvation, led to the suggestion that the pro-9R hydrogen atom of biotin, which is in α-position to the CO2- group, might be changed to a larger group and lead to better binding with streptavidin and avidin. Free energy calculations supported this suggestion and predicted that the methyl analogue should bind ≈3 kcal/mol more tightly to streptavidin, with this difference coming exclusively from the relative desolvation free energy of the ligand. The PROFEC analysis further suggested little or no improvement for changing the pro-9S hydrogen atom to a methyl group, and great reduction in changing the ureido N-H groups to N-CH3. Stimulated by these results, we synthesized 9R-methylbiotin and 9S-methylbiotin, and their binding free energies and enthalpies were measured for interaction with streptavidin and avidin, respectively. In contrast to the calculated results, experiments found both 9-methylbiotin isomers to bind more weakly to streptavidin than biotin. The calculated preference for the binding of the 9R- over the 9S-stereoisomer was observed. In addition, 9-methylbiotin is considerably less soluble in water than biotin, as predicted by the calculation, and the 9R isomer is, to our knowledge, thus far the tightest binding analogue of biotin to streptavidin. Subsequently, X-ray structures of the complexes between streptavidin and both 9R- and 9S-methylbiotin were determined, and the structures were consistent with those used in the free energy calculations. Thus, the reason for the discrepancy between the calculated and experimental binding free energy does not lie in unusual binding modes for the 9-methylbiotins.