2,5-ジアミノ-6-ヒドロキシ-4-(5-ホスホリボシルアミノ)ピリミジン
IUPAC名
[(2R,3S,4R,5R)-5-[(2,5-diamino-4-oxo-1H-pyrimidin-6-yl)amino]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
別称2,5-diamino-6-ribofuranosylamino-4(3H)-pyrimidinone monophosphate; N-(2,5-diamino-6-hydroxypyrimidin-4-yl)-5-O-phosphono-beta-D-ribofuranosylamine
識別情報
PubChem439480
2,5-ジアミノ-6-ヒドロキシ-4-(5-ホスホリボシルアミノ)ピリミジン(2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine)は、プリン代謝の代謝物質で、GTPシクロヒドロラーゼIIによるGTPの加水分解によって形成される[1]。2種類の酵素がこの反応を担う。まずGTPシクロヒドロラーゼIIaが、8,9位の結合を加水分解して2-アミノ-5-ホルミルアミノ-6-(5-ホスホ-D-リボシルアミノ)ピリミジン-4(3H)-オンを形成し[2]、次いで2-アミノ-5-ホルミルアミノ-6-リボシルアミノピリミジン-4(3H)-オン5'-モノリン酸デホルミラーゼによって脱ホルミル化される[3]。2,5-ジアミノ-6-ヒドロキシ-4-(5-ホスホリボシルアミノ)ピリミジンは、ジアミノヒドロキシホスホリボシルアミノピリミジンデアミナーゼによって脱アミノ化され、5-アミノ-6-(5-ホスホリボシルアミノ)ウラシルを形成する[4]。
出典^ Foor F, Brown GM (1975). “Purification and properties of guanosine triphosphate cyclohydrolase II from Escherichia coli”. J. Biol. Chem. 250 (9): 3545–51. .mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation.cs-ja1 q,.mw-parser-output .citation.cs-ja2 q{quotes:"「""」""『""』"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free a,.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited a,.mw-parser-output .id-lock-registration a,.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription a,.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:#d33}.mw-parser-output .cs1-visible-error{color:#d33}.mw-parser-output .cs1-maint{display:none;color:#3a3;margin-left:0.3em}.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}PMID 235552.
^ Graham DE, Xu H, White RH (2002). “A member of a new class of GTP cyclohydrolases produces formylaminopyrimidine nucleotide monophosphates”. Biochemistry. 41 (50): 15074–84. doi:10.1021/bi0268798. PMID 12475257.
^ Grochowski, L.L., Xu, H. and White, R.H. (2009). “An iron(II) dependent formamide hydrolase catalyzes the second step in the archaeal biosynthetic pathway to riboflavin and 7,8-didemethyl-8-hydroxy-5-deazariboflavin”. Biochemistry 48: 4181-4188. PMID 19309161.
^ Burrows RB, Brown GM (1978). “Presence of Escherichia coli of a deaminase and a reductase involved in biosynthesis of riboflavin”. J. Bacteriol. 136 (2): 657–67. PMC 218591. PMID 30756. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC218591/.