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D3385

Sigma-Aldrich

3′-Dephosphocoenzyme A

≥90% (HPLC)

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Synonym(s):
3′-Desphosphocoenzyme A, dpCoA
Empirical Formula (Hill Notation):
C21H35N7O13P2S
CAS Number:
3633-59-8
Molecular Weight:
687.55
MDL number:
MFCD00057010
UNSPSC Code:
41106305
PubChem Substance ID:
24893748
NACRES:
NA.51

Quality Level

200

Assay

≥90% (HPLC)

form

powder

impurities

≤1% CoA

storage temp.

−20°C

SMILES string

CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)n2cnc3c(N)ncnc23)C(O)C(=O)NCCC(=O)NCCS

InChI

1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)

InChI key

KDTSHFARGAKYJN-UHFFFAOYSA-N

Related Categories

Application

3′-Dephosphocoenzyme A has been used as a substrate to initiate transcription.
Dephosphocoenzyme A is the direct precursor of coenzyme A. It is used for the synthesis of coenzyme A by bifunctional CoA Synthase (CoASy, 4′-phosphopantetheine adenylyltransferase/dephospho-CoA kinase) which performs the transfer of the γ-phosphate of ATP to dephosphocoenzyme A.

Biochem/physiol Actions

3′-Dephosphocoenzyme A (DepCoA), also called desphosphoCoA (dpCoA), is synthesized from 4-phosphopantetheine by the enzyme phosphopanthetheine adenylyltransferase. It is an intermediate in coenzyme A biosynthetic pathway. In the presence of dephospho-CoA kinase (CoaE), dephosphocoenzyme A is converted to coenzyme A. 3′-Dephosphocoenzyme shares adenosine-diphosphate substructure as like the purines and is a non-canonical nucleotide and is an initiator of transcription initiation. It is routinely used in in vitro transcription studies to initiate RNA synthesis.

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Guneet Walia et al.
PloS one, 6(1), e15228-e15228 (2011-01-26)
Dephosphocoenzyme A kinase performs the transfer of the γ-phosphate of ATP to dephosphocoenzyme A, catalyzing the last step of coenzyme A biosynthesis. This enzyme belongs to the P-loop-containing NTP hydrolase superfamily, all members of which posses a three domain topology
L Luo et al.
Biochemistry, 40(51), 15684-15692 (2001-12-19)
4-Chlorobenzoyl-coenzyme A (4-CBA-CoA) dehalogenase catalyzes the hydrolytic dehalogenation of 4-CBA-CoA to 4-hydroxybenzoyl-CoA (4-HBA-CoA) via a multistep mechanism involving initial attack of Asp145 on C(4) of the substrate benzoyl ring to form a Meisenheimer intermediate (EMc), followed by expulsion of the
A Geerlof et al.
The Journal of biological chemistry, 274(38), 27105-27111 (1999-09-10)
Phosphopantetheine adenylyltransferase (PPAT) catalyzes the penultimate step in coenzyme A (CoA) biosynthesis: the reversible adenylation of 4'-phosphopantetheine yielding 3'-dephospho-CoA and pyrophosphate. Wild-type PPAT from Escherichia coli was purified to homogeneity. N-terminal sequence analysis revealed that the enzyme is encoded by
The mechanism of RNA 5? capping with NAD+, NADH and desphospho-CoA
Bird JG, et al.
Nature, 535(7612), 444-444 (2016)
CapZyme-Seq Comprehensively Defines Promoter-Sequence Determinants for RNA 5? Capping with NAD+
Vvedenskaya IO, et al.
Molecular Cell, 70(3), 553-564 (2018)
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