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Key Documents

D3385

Sigma-Aldrich

3′-Dephosphocoenzyme A

≥90% (HPLC)

Synonyme(s) :

3′-Desphosphocoenzyme A, dpCoA

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About This Item

Formule empirique (notation de Hill):
C21H35N7O13P2S
Numéro CAS:
Poids moléculaire :
687.55
Numéro MDL:
Code UNSPSC :
41106305
ID de substance PubChem :
Nomenclature NACRES :
NA.51

Niveau de qualité

Pureté

≥90% (HPLC)

Forme

powder

Impuretés

≤1% CoA

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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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