start-ver=1.4 cd-journal=joma no-vol=20 cd-vols= no-issue=Special Issue article-no= start-page=36 end-page=41 dt-received= dt-revised= dt-accepted= dt-pub-year=2009 dt-pub=200912 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of a Representative, Natural Pterin Glycoside: 2f-O-(-D-Glucopyranosyl)biopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=Glycosylation of N(2)-(N,N-dimethylaminomethylene)-1f-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl) ethyl]biopterin (14) with the novel donor 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)--D-glucopyranosyl bromide (19) in the presence of silver triflate and tetramethylurea predominantly afforded the corresponding -D-glucopyranoside (20a), from which 2f-O-(-D-glucopyranosyl)biopterin (1) was obtained by the successive removal of the protecting groups. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=PfleidererWolfgang en-aut-sei=Pfleiderer en-aut-mei=Wolfgang kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=School of Pharmacy, Shujitsu University affil-num=3 en-affil= kn-affil=Fachbereich Chemie, Universit?t Konstanz en-keyword=biopterin D-glucoside kn-keyword=biopterin D-glucoside en-keyword=pterin glycoside kn-keyword=pterin glycoside en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting groups kn-keyword=protecting groups END start-ver=1.4 cd-journal=joma no-vol=21 cd-vols= no-issue=3 article-no= start-page=79 end-page=83 dt-received= dt-revised= dt-accepted= dt-pub-year=2010 dt-pub=201009 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of a Natural Neopterin Glycoside: 3'-O-(-D-Glucopyranosyluronic acid)neopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=1',2'-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]neopterin (1) was prepared from neopterin in 5 steps. Glycosylation of 1 with methyl 2,3,4-tri-O-benzoyl--D-glucopyranosyluronate bromide in the presence of silver triflate and tetramethylurea afforded the corresponding 3'-O-(methyl -D-glucopyranosyluronate) neopterin derivative (2) in 64% yield. The first synthesis of 3'-O-(-D-glucopyranosyluronic acid)neopterin was achieved by successive removal (4 steps) of the protecting groups of 2. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=HattoriTakafumi en-aut-sei=Hattori en-aut-mei=Takafumi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=TakayamaDaisuke en-aut-sei=Takayama en-aut-mei=Daisuke kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=neopterin glycoside kn-keyword=neopterin glycoside en-keyword=D-glucronic acid kn-keyword=D-glucronic acid en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting groups kn-keyword=protecting groups END start-ver=1.4 cd-journal=joma no-vol=24 cd-vols= no-issue=1 article-no= start-page=3 end-page=6 dt-received= dt-revised= dt-accepted= dt-pub-year=2013 dt-pub=201306 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of Asperopterin A, an Isoxanthopterin Glycoside from Aspergillus Oryzae en-subtitle= kn-subtitle= en-abstract= kn-abstract=The key precursor, N-2-(N,N -dimethylaminomethylene)-6-hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding beta-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b). en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= affil-num=1 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=2 en-affil= kn-affil=Shujitsu Univ, Sch Pharm en-keyword=asperopterin kn-keyword=asperopterin en-keyword=glycosylation kn-keyword=glycosylation en-keyword=isoxanthopterin kn-keyword=isoxanthopterin en-keyword=protecting groups kn-keyword=protecting groups en-keyword=pterin glycoside kn-keyword=pterin glycoside END start-ver=1.4 cd-journal=joma no-vol=19 cd-vols= no-issue=3 article-no= start-page=72 end-page=78 dt-received= dt-revised= dt-accepted= dt-pub-year=2008 dt-pub=200809 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=An Efficient Synthesis of 2'-O-(-D-Ribofuranosyl)biopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=N(2)-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O (trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl- D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2'-O-(2,3,5-tri-Oacetyl- and 2,3,5-tri-O-benzoyl--D ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2'-O-(-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=TorigoeKiyoshi en-aut-sei=Torigoe en-aut-mei=Kiyoshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=SoranakaKazuyuki en-aut-sei=Soranaka en-aut-mei=Kazuyuki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=FujitaHiroshi en-aut-sei=Fujita en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=PfleidererWolfgang en-aut-sei=Pfleiderer en-aut-mei=Wolfgang kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=5 en-affil= kn-affil=School of Pharmacy, Shujitsu University affil-num=6 en-affil= kn-affil=Fachbereich Chemie, Universit?t Konstanz en-keyword=biopterin D-riboside kn-keyword=biopterin D-riboside en-keyword=pterin glycoside kn-keyword=pterin glycoside en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting groups kn-keyword=protecting groups END