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Key Documents

D3385

Sigma-Aldrich

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:
Molecular Weight:
687.55
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

Quality Level

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

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 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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The mechanism of RNA 5? capping with NAD+, NADH and desphospho-CoA
Bird JG, et al.
Nature, 535(7612), 444-444 (2016)
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
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)
Azusa Seto et al.
Proteins, 58(1), 235-242 (2004-11-05)
Dephosphocoenzyme A kinase (DCK) catalyzes phosphorylation in the final step of coenzyme A (CoA) biosynthesis. In this phosphorylation process, domain movements play a very important role. To reveal the structural changes induced by ligand binding, we determined the crystal structure

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