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Adenylosuccinate - Wikipedia

From Wikipedia, the free encyclopedia

Adenylosuccinate
Names

IUPAC name (2S)-2-[[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid
Identifiers
CAS Number	19046-78-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15919^Y
ChemSpider	389122^Y
MeSH	Adenylosuccinate
PubChem CID	447145
UNII	X1B4ZJ0IIV^Y
InChI InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1^Y Key: OFBHPPMPBOJXRT-DPXQIYNJSA-N^Y InChI=1/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1 Key: OFBHPPMPBOJXRT-DPXQIYNJBG
SMILES C1=NC2=C(C(=N1)N[C@@H](CC(=O)O)C(=O)O)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O
Properties
Chemical formula	C₁₄H₁₈N₅O₁₁P
Molar mass	463.296 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Adenylosuccinate, also known as succinyl-adenosine monophosphate (S-AMP), is an intermediate in the interconversion of purine nucleotides inosine monophosphate (IMP) and adenosine monophosphate (AMP). The enzyme adenylosuccinate synthase carries out the reaction of IMP to S-AMP in a 2 step mechanism,^[1] requiring the input of energy from a phosphoanhydride bond from the hydrolysis of guanosine triphosphate (GTP)^[2] first, followed by the addition of aspartate. This reaction needs Mg²⁺,^[3] and is competitively inhibited by the subsequent product AMP^[3] in a negative feedback mechanism.^[4] GTP, the product of another pathway from IMP, is used instead of adenosine triphosphate (ATP) as the phosphate source. The enzyme adenylosuccinate lyase carries out the reaction removing the carbon skeleton from S-AMP attached from aspartate, forming AMP and fumarate.^[4] The pathway from IMP to AMP is present across various prokaryotes and eukaryotes, and is linked to various diseases.^[5] S-AMP has been observed to stimulate insulin production.^[6]

References

^ Mehrotra, Sonali; Balaram, Hemalatha (2007-11-06). "Kinetic characterization of adenylosuccinate synthetase from the thermophilic archaea Methanocaldococcus jannaschii". Biochemistry. 46 (44): 12821–12832. doi:10.1021/bi701009y. ISSN 0006-2960. PMID 17929831.
^ Figures 20.4 and 20.7 in Textbook of Biochemistry, with clinical correlations, Sixth Edition, Thomas M. Devlin, Ed., Wiley-Liss, Inc., New York, NY, 2006
^ ^a ^b Iancu, Cristina V.; Borza, Tudor; Fromm, Herbert J.; Honzatko, Richard B. (2002-10-25). "Feedback inhibition and product complexes of recombinant mouse muscle adenylosuccinate synthetase". The Journal of Biological Chemistry. 277 (43): 40536–40543. doi:10.1074/jbc.M204952200. ISSN 0021-9258. PMID 12186864.
^ ^a ^b Garrett, Reginald H.; Grisham, Charles M. (2017). Biochemistry (6th ed.). Boston, MA: Cengage Learning. pp. 927–940. ISBN 978-1-305-57720-6.
^ Marsac, Roxane; Pinson, Benoît; Saint-Marc, Christelle; Olmedo, María; Artal-Sanz, Marta; Daignan-Fornier, Bertrand; Gomes, José-Eduardo (2019). "Purine Homeostasis Is Necessary for Developmental Timing, Germline Maintenance and Muscle Integrity in Caenorhabditis elegans". Genetics. 211 (4): 1297–1313. doi:10.1534/genetics.118.301062. ISSN 1943-2631. PMC 6456310. PMID 30700528.
^ Gooding, Jessica R.; Jensen, Mette V.; Dai, Xiaoqing; Wenner, Brett R.; Lu, Danhong; Arumugam, Ramamani; Ferdaoussi, Mourad; MacDonald, Patrick E.; Newgard, Christopher B. (2015-10-06). "Adenylosuccinate Is an Insulin Secretagogue Derived from Glucose-Induced Purine Metabolism". Cell Reports. 13 (1): 157–167. doi:10.1016/j.celrep.2015.08.072. ISSN 2211-1247. PMC 4598307. PMID 26411681.

Nucleotide metabolic intermediates

purine
metabolism

anabolism

R5P→IMP:	Ribose 5-phosphate (R5P) Phosphoribosyl pyrophosphate (PRPP) Phosphoribosylamine (PRA) Glycineamide ribonucleotide (GAR) Phosphoribosyl-N-formylglycineamide (FGAR) 5′-Phosphoribosylformylglycinamidine (FGAM) 5-Aminoimidazole ribotide (AIR) 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole (CAIR) Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) AICA ribonucleotide (AICAR) 5-Formamidoimidazole-4-carboxamide ribotide (FAICAR)
IMP→AMP:	Adenylosuccinate
IMP→GMP:	Xanthosine monophosphate

catabolism

pyrimidine
metabolism

anabolism

catabolism

uracil:	β-Alanine Dihydrouracil 3-Ureidopropionic acid
thymine:	3-Aminoisobutyric acid Dihydrothymine β-Ureidoisobutyric acid

Category:

Nucleotides

Hidden categories:

See also

References