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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
Form:
powder
Assay:
≥90% (HPLC)
Solubility:
H2O: soluble-50 mg/mL, clear to slightly hazy, colorless to faintly yellow
Biological source:
synthetic (organic)
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biological source

synthetic (organic)

Quality Level

200

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

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

Application

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.
3′-Dephosphocoenzyme A has been used as a substrate to initiate transcription.

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.

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This Item
A6904A9501D134406
3′-Dephosphocoenzyme A ≥90% (HPLC)

Sigma-Aldrich

D3385

3′-Dephosphocoenzyme A

Adenosine 5′-diphosphate, periodate oxidized sodium salt 90-95%

Sigma-Aldrich

A6904

Adenosine 5′-diphosphate, periodate oxidized sodium salt

Adenosine 3′,5′-cyclic monophosphate ≥98.5% (HPLC), powder

Sigma-Aldrich

A9501

Adenosine 3′,5′-cyclic monophosphate

3′,5′-Dimethoxy-4′-hydroxyacetophenone 97%

Sigma-Aldrich

D134406

3′,5′-Dimethoxy-4′-hydroxyacetophenone

solubility

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

solubility

-

solubility

H2O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)

solubility

-

assay

≥90% (HPLC)

assay

90-95%

assay

≥98.5% (HPLC)

assay

97%

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

form

powder

form

solid

form

powder

form

solid

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
0000562672
0000562672
0000516180
0000516179
0000516180

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Efficient one-pot enzymatic synthesis of dephospho coenzyme A
Sapkota K and Huang F
Bioorganic Chemistry, 76, 23-27 (2018)
Thomas J Wubben et al.
Journal of molecular biology, 404(2), 202-219 (2010-09-21)
Phosphopantetheine adenylyltransferase (PPAT) catalyzes the penultimate step in the coenzyme A (CoA) biosynthetic pathway, reversibly transferring an adenylyl group from ATP to 4'-phosphopantetheine (PhP) to form dephosphocoenzyme A. This reaction sits at the branch point between the de novo pathway
RNA capping by transcription initiation with non-canonical initiating nucleotides (NCINs): determination of relative efficiencies of transcription initiation with NCINs and NTPs
Bird JG, et al.
Bio-protocol, 7(12) (2017)
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Global Trade Item Number

SKUGTIN
D3385-25MG04061833261361
D3385-5MG04061833261378

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