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Key Documents

C0884

Sigma-Aldrich

Coenzyme B12

≥97.0%

Synonym(s):

5′-Deoxyadenosylcobalamine, Adenosyl cobalamine, Cobamamide, DMBC coenzyme

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About This Item

Empirical Formula (Hill Notation):
C72H100CoN18O17P
CAS Number:
Molecular Weight:
1579.58
Beilstein:
4122932
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.79

Assay

≥97.0%

form

powder and chunks

technique(s)

HPLC: suitable

color

red to very dark red
very dark red-brown

storage temp.

−20°C

SMILES string

CC(CNC(=O)CCC1(C)C(CC(N)=O)C2N([Co+]C[C@H]3O[C@@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)C1=C(C)C6=NC(=CC7=NC(=C(C)C8=NC2(C)C(C)(CC(N)=O)C8CCC(N)=O)C(C)(CC(N)=O)C7CCC(N)=O)C(C)(C)C6CCC(N)=O)OP([O-])(=O)O[C@H]9[C@@H](O)[C@H](O[C@@H]9CO)n%10cnc%11cc(C)c(C)cc%10%11

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

InChI key

ZIHHMGTYZOSFRC-PMDPKNCCSA-L

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General description

Vitamin B12 cobalamin refers to a group of chemically-related cobalt containing molecules. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms.

Application

Coenzyme B12 has been used as a supplement for culturing plasmid variants in in vivo assay of yvrC-lacZ fusions.

Biochem/physiol Actions

Vitamin B12 cobalamin is involved in DNA synthesis and fatty acid synthesis. It also plays a vital role as a coenzyme in the conversion of mitochondrial methylmalonyl co-enzyme A to succinyl co-enzyme A.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Coenzyme B12 riboswitches are widespread genetic control elements in prokaryotes
Nahvi A, et al.
Nucleic Acids Research, 32(1), 143-150 (2004)
Claire Chatelle et al.
ACS synthetic biology, 7(5), 1349-1358 (2018-04-11)
The ever-increasing complexity of synthetic gene networks and applications of synthetic biology requires precise and orthogonal gene expression systems. Of particular interest are systems responsive to light as they enable the control of gene expression dynamics with unprecedented resolution in
Radical catalysis in coenzyme B12-dependent isomerization (eliminating) reactions.
Tetsuo Toraya
Chemical reviews, 103(6), 2095-2127 (2003-06-12)
Gregory M Sandala et al.
Accounts of chemical research, 43(5), 642-651 (2010-02-09)
Enzymes accelerate chemical reactions with an exceptional selectivity that makes life itself possible. Understanding the factors responsible for this efficient catalysis is of utmost importance in our quest to harness the tremendous power of enzymes. Computational chemistry has emerged as
Alla Peselis et al.
Nature structural & molecular biology, 19(11), 1182-1184 (2012-10-16)
Coenzyme B(12) has a key role in various enzymatic reactions and controls expression of bacterial genes through riboswitches. Here we report the crystal structure of the Symbiobacterium thermophilum B(12) riboswitch bound to its ligand adenosylcobalamin. The riboswitch forms a unique

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