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Merck
CN

D3385

3′-Dephosphocoenzyme A

≥90% (HPLC)

Synonym(s):

3′-Desphosphocoenzyme A, dpCoA

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About This Item

Empirical Formula (Hill Notation):
C21H35N7O13P2S
CAS Number:
3633-59-8
Molecular Weight:
687.55
NACRES:
NA.51
PubChem Substance ID:
24893748
UNSPSC Code:
41106305
MDL number:
MFCD00057010

Key Documents

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Product Name

3′-Dephosphocoenzyme A, ≥90% (HPLC)

InChI key

KDTSHFARGAKYJN-UHFFFAOYSA-N

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)

biological source

synthetic (organic)

assay

≥90% (HPLC)

form

powder

impurities

≤1% CoA

solubility

H2O: soluble-50 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

−20°C

Quality Level

200

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000516180
0000516179
0000516180
0000516179
0000476945

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Efficient incorporation of CoA, NAD and FAD into RNA by in vitro transcription
Huang F
Nucleic Acids Research, 31(3), e8-e8 (2003)
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
CapZyme-Seq Comprehensively Defines Promoter-Sequence Determinants for RNA 5? Capping with NAD+
Vvedenskaya IO, et al.
Molecular Cell, 70(3), 553-564 (2018)
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
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