Adenosylcobalamin

Adenosylcobalamin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	B03BA04 (WHO) ;
Legal status
Legal status	US: OTC ;
Identifiers
	IUPAC name Coα-[α-(5,6-dimethylbenzimidazolyl)]-Coβ-; (5'-deoxy-5'-adenosyl)cobamide;
CAS Number	13870-90-1 ;
PubChem CID	5459907;
ChemSpider	16736117 ;
KEGG	D00042 ;
ChEBI	CHEBI:18408 ;
ECHA InfoCard	100.034.192
Chemical and physical data
Formula	C72H100CoN18O17P
Molar mass	1579.58 g/mol g·mol−1
	InChI InChI=1S/C62H90N13O14P.C10H12N5O3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31?,34?,35?,36?,37?,41-,52-,53-,56?,57+,59?,60?,61?,62?;4-,6-,7-,10-;/m11./s1 ; Key:ZIHHMGTYZOSFRC-CXGXMSGESA-L ;
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Adenosylcobalamin (AdoCbl), also known as coenzyme B₁₂, cobamamide, and dibencozide, is, along with methylcobalamin (MeCbl), one of the biologically active forms of vitamin B₁₂.[1]

Adenosylcobalamin participates as a cofactor in radical-mediated 1,2-carbon skeleton rearrangements. These processes require the formation of the deoxyadenosyl radical through homolytic dissociation of the carbon-cobalt bond. This bond is exceptionally weak, with an bond dissociation energy of 31 kcal/mol, which is further lowered in the chemical environment of an enzyme active site.[2] An enzyme that uses adenosylcobalamin as a cofactor is methylmalonyl-CoA mutase (MCM).

References

Marsh EN, Meléndez GD (November 2012). "Adenosylcobalamin enzymes: theory and experiment begin to converge". Biochimica et Biophysica Acta. 1824 (11): 1154–64. doi:10.1016/j.bbapap.2012.03.012. PMC 3580769. PMID 22516318.
Kräutler B, Arigoni D, Golding BT (1998). Vitamin B12 and B12-proteins : lectures presented at the 4th European Symposium on Vitamin B12 and B12-Proteins. Weinheim: Wiley-VCH. ISBN 9783527612192. OCLC 212131311.

External links

B03BA04 (WHO)

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[1] Marsh EN, Meléndez GD (November 2012). "Adenosylcobalamin enzymes: theory and experiment begin to converge". Biochimica et Biophysica Acta. 1824 (11): 1154–64. doi:10.1016/j.bbapap.2012.03.012. PMC 3580769. PMID 22516318.

[2] Kräutler B, Arigoni D, Golding BT (1998). Vitamin B12 and B12-proteins : lectures presented at the 4th European Symposium on Vitamin B12 and B12-Proteins. Weinheim: Wiley-VCH. ISBN 9783527612192. OCLC 212131311.