Phosphoribosylamine

Phosphoribosylamine
Names
	Other names PRA
Identifiers
CAS Number	14050-66-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17284;
ChemSpider	2339538;
MeSH	Phosphoribosylamine
PubChemCID	3082052;
CompTox Dashboard(EPA)	DTXSID10903977;
	InChI InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5?/m1/s1 Key: SKCBPEVYGOQGJN-SOOFDHNKSA-N;
	SMILES C([C@@H]1[C@H]([C@H](C(O1)N)O)O)OP(=O)(O)O;
Properties
Chemical formula	C5H12NO7P
Molar mass	229.125 g/mol
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). Infobox references

Phosphoribosylamine(PRA) is a biochemical intermediate in the formation ofpurine nucleotidesviainosine-5-monophosphate, and hence is a building block forDNAandRNA.^[1]^[2]^[3]The vitaminsthiamine^[4]andcobalamin^[5]also contain fragments derived from PRA.^[6]

It is the product of the enzymeamidophosphoribosyltransferasewhich attachesammoniafromglutaminetophosphoribosyl pyrophosphate(PRPP) at itsanomeric carbon:^[2]

PRPP+glutamine→PRA+glutamate+ PPi

The biosynthesis pathway nextcombinesPRA withglycinein a process driven byATPgivingglycineamide ribonucleotide(GAR). The enzymephosphoribosylamine—glycine ligasecatalyses the reaction forming anamidebond:^[7]

PRA+glycine+ ATP →GAR+ ADP + Pi

References

^R. Caspi (2009-01-13)."Pathway: 5-aminoimidazole ribonucleotide biosynthesis I".MetaCyc Metabolic Pathway Database.Retrieved2022-02-02.
^^a ^bZhang, Y.; Morar, M.; Ealick, S.E. (2008)."Structural biology of the purine biosynthetic pathway".Cellular and Molecular Life Sciences.65:3699–3724.doi:10.1007/s00018-008-8295-8.PMC2596281.PMID 18712276.
^Gupta, Rani; Gupta, Namita (2021). "Nucleotide Biosynthesis and Regulation".Fundamentals of Bacterial Physiology and Metabolism.pp. 525–554.doi:10.1007/978-981-16-0723-3_19.ISBN 978-981-16-0722-6.S2CID 234897784.
^Chatterjee, Abhishek; Hazra, Amrita B.; Abdelwahed, Sameh; Hilmey, David G.; Begley, Tadhg P. (2010)."A" Radical Dance "in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase".Angewandte Chemie International Edition.49(46): 8653–8656.doi:10.1002/anie.201003419.PMC3147014.PMID 20886485.
^R. Caspi (2019-09-23)."Pathway: 5-hydroxybenzimidazole biosynthesis (anaerobic)".MetaCyc Metabolic Pathway Database.Retrieved2022-02-10.
^Mehta, Angad P.; Abdelwahed, Sameh H.; Fenwick, Michael K.; Hazra, Amrita B.; Taga, Michiko E.; Zhang, Yang; Ealick, Steven E.; Begley, Tadhg P. (2015)."Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis".Journal of the American Chemical Society.137(33): 10444–10447.doi:10.1021/jacs.5b03576.PMC4753784.PMID 26237670.
^Welin, Martin; Grossmann, Jörg Günter; Flodin, Susanne; Nyman, Tomas; Stenmark, Pål; Trésaugues, Lionel; Kotenyova, Tetyana; Johansson, Ida; Nordlund, Pär; Lehtiö, Lari (2010)."Structural studies of tri-functional human GART".Nucleic Acids Research.38(20): 7308–7319.doi:10.1093/nar/gkq595.PMC2978367.PMID 20631005.

[IMP-1] R. Caspi (2009-01-13)."Pathway: 5-aminoimidazole ribonucleotide biosynthesis I".MetaCyc Metabolic Pathway Database.Retrieved2022-02-02.

[Zhang-2] Zhang, Y.; Morar, M.; Ealick, S.E. (2008)."Structural biology of the purine biosynthetic pathway".Cellular and Molecular Life Sciences.65:3699–3724.doi:10.1007/s00018-008-8295-8.PMC2596281.PMID 18712276.

[3] Gupta, Rani; Gupta, Namita (2021). "Nucleotide Biosynthesis and Regulation".Fundamentals of Bacterial Physiology and Metabolism.pp. 525–554.doi:10.1007/978-981-16-0723-3_19.ISBN 978-981-16-0722-6.S2CID 234897784.

[Dance-4] Chatterjee, Abhishek; Hazra, Amrita B.; Abdelwahed, Sameh; Hilmey, David G.; Begley, Tadhg P. (2010)."A" Radical Dance "in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase".Angewandte Chemie International Edition.49(46): 8653–8656.doi:10.1002/anie.201003419.PMC3147014.PMID 20886485.

[HBI-5] R. Caspi (2019-09-23)."Pathway: 5-hydroxybenzimidazole biosynthesis (anaerobic)".MetaCyc Metabolic Pathway Database.Retrieved2022-02-10.

[Begley2015-6] Mehta, Angad P.; Abdelwahed, Sameh H.; Fenwick, Michael K.; Hazra, Amrita B.; Taga, Michiko E.; Zhang, Yang; Ealick, Steven E.; Begley, Tadhg P. (2015)."Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis".Journal of the American Chemical Society.137(33): 10444–10447.doi:10.1021/jacs.5b03576.PMC4753784.PMID 26237670.

[GART-7] Welin, Martin; Grossmann, Jörg Günter; Flodin, Susanne; Nyman, Tomas; Stenmark, Pål; Trésaugues, Lionel; Kotenyova, Tetyana; Johansson, Ida; Nordlund, Pär; Lehtiö, Lari (2010)."Structural studies of tri-functional human GART".Nucleic Acids Research.38(20): 7308–7319.doi:10.1093/nar/gkq595.PMC2978367.PMID 20631005.

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See also

References