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M9131

Sigma-Aldrich

2′-O-Monosuccinyladenosine 3′:5′-cyclic monophosphate

≥98%

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About This Item

Empirical Formula (Hill Notation):
C14H16N5O9P
CAS Number:
36940-87-1
Molecular Weight:
429.28
EC Number:
253-284-5
UNSPSC Code:
41106305
PubChem Substance ID:
24897315

biological source

synthetic (organic)

Quality Level

200

assay

≥98%

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[H][C@@]1(C2)[C@@](O[C@@H](N3C=NC4=C(N)N=CN=C43)[C@@H]1OC(CCC(O)=O)=O)([H])CCP2(O)=O

InChI

1S/C14H16N5O9P/c15-12-9-13(17-4-16-12)19(5-18-9)14-11(27-8(22)2-1-7(20)21)10-6(26-14)3-25-29(23,24)28-10/h4-6,10-11,14H,1-3H2,(H,20,21)(H,23,24)(H2,15,16,17)

InChI key

QNPSLGPIZRJDAN-UHFFFAOYSA-N

Application

2′-O-Monosuccinyladenosine 3′:5′-cyclic monophosphate is a cAMP analog that may be used with other cAMP analogs to evaluate cAMP mediate processes within cells.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Vinay Bulusu et al.
Biochimica et biophysica acta, 1794(4), 642-654 (2008-12-30)
Adenylosuccinate lyase (ASL) catalyzes two distinct but chemically similar reactions in purine biosynthesis. The first, exclusive to the de novo pathway involves the cleavage of 5-aminoimidazole-4-(N-succinylcarboxamide) ribonucleotide (SAICAR) to 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) and fumarate and the second common to both
R A Richman et al.
Journal of cyclic nucleotide research, 6(6), 461-468 (1980-01-01)
Antisera to cyclic AMP and cyclic GMP were obtained by immunizing rabbits with antigens prepared by conjugating the 2'0-succinyl derivative of the cyclic nucleotides to thyroglobulin. The cyclic nucleotide-thyroglobulin conjugates were injected intradermally into multiple sites on the backs of
Michael Newton et al.
Analytical biochemistry, 402(2), 129-136 (2010-04-08)
Nitric oxide (NO) mediates intercellular signaling through activation of its receptor, soluble guanylyl cyclase (sGC), leading to elevation of intracellular guanosine 3',5'-cyclic monophosphate (cGMP) levels. Through this signal transduction pathway, NO regulates a diverse range of physiological effects, from vasodilatation
S C Wen et al.
Endocrinology, 116(3), 935-944 (1985-03-01)
Adrenal cortical cells are known to export cAMP and have binding proteins and cAMP-dependent protein kinase activity associated with their plasma membranes. Because these properties suggest a function for extracellular cAMP, we have undertaken a search for specific cell surface
Linda Aumo et al.
Endocrinology, 151(5), 2151-2161 (2010-03-18)
In the adrenal cortex, the biosynthesis of steroid hormones is controlled by the pituitary-derived hormone ACTH. The functions of ACTH are principally relayed by activating cAMP-dependent signaling pathways leading to the induction of genes encoding enzymes involved in the conversion
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