InChI=1S/C10H16N2O5S/c13-8(14)4-2-1-3-7-9-6(5-18(7,16)17)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1 |
QPFQYMONYBAUCY-ZKWXMUAHSA-N |
[H][C@]12CS(=O)(=O)[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2 |
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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View more via ChEBI Ontology
5-[(3aS,4S,6aR)-5,5-dioxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
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5,5-Dioxide Biotin
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HMDB
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[3aS-(3aa,4b,6aa)]-5,5-dioxide-hexahydro-2-oxo-1H-Thieno[3,4-D]imidazole-4-pentanoic acid
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HMDB
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33724
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Reaxys Registry Number
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Reaxys
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40720-05-6
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CAS Registry Number
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ChemIDplus
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Collot M, Sendid B, Fievez A, Savaux C, Standaert-Vitse A, Tabouret M, Drucbert AS, Danzé PM, Poulain D, Mallet JM (2008) Biotin sulfone as a new tool for synthetic oligosaccharide immobilization: application to multiple analysis profiling and surface plasmonic analysis of anti-Candida albicans antibody reactivity against alpha and beta (1-->2) oligomannosides. Journal of medicinal chemistry 51, 6201-6210 [PubMed:18788729] [show Abstract] As a part of our glycoantigen synthetic program for diagnosis and basic analysis of yeast-related pathogenic mechanisms, a library of 1-->2 oligomannosides suitable for immunoanalysis was prepared. The use of biotin sulfone, an oxidized form of biotin, offers a convenient solution for both oligosaccharide synthesis and immobilization on microspheres and surface plasmon resonance sensors. The application of this new strategy for the analysis of anti- Candida albicans antibody response through multiple-analyte profiling technology (Luminex) and with surface plasmonic analysis using biotin tagged synthetic oligosaccharides on avidin coated surfaces was validated using monoclonal antibodies. | Zempleni J, McCormick DB, Mock DM (1997) Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-l-sulfoxide in human urine. The American journal of clinical nutrition 65, 508-511 [PubMed:9022537] [show Abstract] In previous studies using the HPLC and avidin-binding assay, five unidentified avidin-binding substances were observed in human urine. The present study investigated the identity of these substances. Urine was collected before and after intravenous administration of 18.5 mumol biotin to healthy adults. Unknown substances 1 and 3 were initially identified as biotin sulfone and bisnorbiotin methyl ketone, respectively, by coelution with authentic standards on HPLC. Identities were confirmed by thin-layer chromatography and by derivatization with p-dimethyl-aminocinnamaldehyde. As expected for biotin metabolites, the urinary excretion of biotin sulfone and bisnorbiotin methyl ketone increased with biotin administration. The urinary excretion of biotin sulfone increased 21-fold from 0.2 nmol/h before to 4.2 nmol/h after administration; the excretion of bisnorbiotin methyl ketone increased 130-fold from 0.4 to 51.8 nmol/h. At presumed steady state in free-living subjects (n = 6), biotin sulfone and bisnorbiotin methyl ketone accounted for 3.6% and 7.9% of total biotin excretion, respectively. Traces of tetranorbiotin-l-sulfoxide were also identified by using thin-layer chromatography and derivatization with p-dimethylaminocinnamaldehyde. However, tetranorbiotin-l-sulfoxide was not detectable in urine by the HPLC and avidin-binding assay because this metabolite has weak avidin-binding affinity. We conclude that biotin sulfone and bisnorbiotin methyl ketone are present in measurable quantities in human urine; their quantitation should allow more accurate studies on human biotin metabolism and turnover. | PELLEGRINO G (1957) [Effects of biotin sulfone on disposition toward experimental reflex epilepsy]. Bollettino della Societa italiana di biologia sperimentale 33, 1191-1192 [PubMed:13510484] | RAVEL JM, SHIVE W (1955) A study of biotin sulfone inhibition of Lactobacillus arabinosus. Archives of biochemistry and biophysics 54, 341-348 [PubMed:14350781] | RUBIN SH, SCHEINER J (1949) Antibiotin effect of homologs of biotin and biotin sulfone. Archives of biochemistry 23, 400-410 [PubMed:18141516] | AXELROD AE, DeWOODY J, HOFMANN K (1946) The differential effect of biotin sulfone and gamma-(3,4-ureylenecyclohexyl) butyric acid upon the microbiological activity of biotin and oxybiotin. The Journal of biological chemistry 163, 771 [PubMed:20985652] |
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