多糖磷酸酯化的研究进展

20022211,835～839ChineseJournalofOrganicChemistryVol.22,2002No.11,835～839··陈晓明　　田庚元(　200032)　.　,,AdvancesinStudiesonPhosphorylationofPolysaccharidesCHEN,Xiao-Ming　　TIAN,Geng-Yuan(StateKeyLaboratoryofBio-organic&NaturalProductsChemistry,ShanghaiInstituteofOrganicChemistry,ChineseAcademyofSciences,Shanghai20032)Abstract　Thispaperreviewstherecentprogressinphosphateofsaccharideandthemethodsofpreparingtheirderivative.Keywords　polysaccharide,phosphate,phosphorylation　　,(、),.、,,,、、、、.,,.70,,,,.、、、.、[1].,.、、、,.Nakashima[2],,[3].(HIV)[4]..β-(1※6)-D-,,[5].,,O-O-;,、ICR-JCLErhlich[6].,、、、、,.E-mail:[e-mail]27,2001;revisedJanuary15,2002;acceptedMarch30,2002.,,、,,,.1　,.,[7]Enterococcusfaecalis()、.VanCasteren[8]Trichodermaviride()、、.Severn[9]Mycobacteriumbovis().Parolis[10]Pichiaholstii().,,,,.,、,,,、.,[11].[12]、、[13][14].、、,.1988Hayachi[15]、,.[16]、[17]、[18][19].[20]N,N-(2-)L1210S-180.,.Suzuki[21]S-180.α-(1※6),.,,.Inoue[22],,,,.,.[23].Williams[24]β-(1※3)-D-,.,,.,,,、.、,,,.,、,,,,.;.2　、.,;,.、,,0.01～0.4.:2.1　.,,,...Williams[24].70%,2.23%,0.13.,836　　　　　　Vol.22,2002.,,,,,,,,.,.、、.,.,.,,,,.,,、,.,,,.2.2　、,.,..、、、.,,.pH,,.,0.05,,.[23]pH2.0.25,0.013.,,,0.05..2.3　(P3m)P3m.、、、,.P3m,pH,,,,2～3(,).P3m,,,、,,.P3m、、.,Hideko[25]P3m,,pH12,24h、,1-,..Mitsutom[26]P3m6-,1-.,P3m.Hideko[27]P3m,0.03.P3m,,.2.4　,,,,,、,,..,,.POCl3,,POCl3、DMF、,,.,,,.Sang-AhLee[28],NaOHpH12,45℃3h.β-.5.67%,0.38.,,,,.,.,0.9..Kim[29]6-,6′-.POCl3、,,,,,837No.11:　,.,,、,.,,,,.,、,,.,,.2.5　、、、.,....,,、.,、.3　,.,.,,,.,.,.,,;,、、,、..,,,.、,.,,、、、、、、、、,,,、..、、.References1　(a)Alper,J.Science2001,291,2338.(b)Rudd,P.M.;Elliott,T.;Cresswell,P.;Wilson,L.A.;Dwek,R.A.Science2001,291,2370.(c)Helenius,A.;Aebi,M.Science2001,291,2364.(d)Ma,Y.-Q.;Geng,J.-G.J.Immunol.2000,165,558.(e)Franz,G.PlantaMed.1989,55,493.2　Nakashima,H.;Kido,Y.;Kobayashi,N.;Motoki,Y.;Neushul,M.;Yamamoto,N.J.CancerRes.Clin.Oncol.1987,113,413.3　Sugawara,I.;Ishizaka,S.AgentsActions1983,13,345.4　Yoshida,O.;Nakashima,H.;Yoshida,T.;Kaneko,Y.;Yamamoto,I.;Matsuzaki,K.;Uryu,T.;Yamamoto,N.Biochem.Pharmcol.1988,37,2887.5　Huang,F.;Meng,Y.-W.Nat.Prod.Res.Dev.1999,11(5),90(inChinese).　　(,,天然产物研究与开发,1999,11(5),90.)6　Shiio,T.;Yoshihama,T.;Yugari,Y.Brit.GB1509587,1978[Chem.Abstr.1978,89,169090].7　Wang,Y.;Johannes,H.;Arthur,O.Carbohydr.Res.1999,316,155.8　VanCasteren,W.H.M.;Kabel,M.A.;Dijkema,C.;Schols,H.A.;Beldman,G.;Voragen,A.G.J.Carbohydr.Res.1999,317,131.9　Seven,W.B.;Furneaux,R.H.;Falshaw,R.;Atkinson,P.H.Carbohydr.Res.1998,308,397.10　Parolis,L.A.S.;Parolis,H.;Kenne,L.;Meldal,M.;Bock,K.Carbohydr.Res.1998,309,77.11　Voitenko,A.V.;Volkova,L.V.;Evstigneeva,R.P.Zh.Obshch.Khim.1980,50(9),2140.12　Hasegawa,A.;Kiso,M.;Unger,F.M.Ger.Offen.DE3730905,1988[Chem.Abstr.1989,111,134689].13　Nichima,T.;Soga,T.;Shiba,T.Jpn.KokaiTokkyoKohoJP63183594,1988[Chem.Abstr.1989,110,135648].14　Macher,I.Eur.Pat.Appl.EP309411,1989[Chem.Abstr.1989,111,174596].15　Hayauchi,Y.;Lockhoff,O.;babczinski,P.;Petzinna,D.;Bischoff,H.Ger.Offen.DE3631004,1988[Chem.838　　　　　　Vol.22,2002Abstr.1989,110,135656].16　Yang,X.-F.;Zhang,H.-J.;Qin,S.-L.;Zhao,C.-J.;Xiao,T.-R.NewDrugsandClinicalRemendies1996,15(2),69(inChinese).　　(,,,,,新药与临床,1996,15(2),69.)17　Wang,S.-Y.;Dai,R.-H.;Xu,J.-M.;Zheng,H.-J.;Chen,S.-X.;Chen,M.-F.;Xu,H.-F.;Zhao,M.-H.;Rong,Y.-Z.NewDrugsandClinicalRemendies1997,16(2),66(inChinese).　　(,,,,,,,,,新药与临床,1997,16(2),66.)18　Zhao,J.-B.;Zhang,Y.-L.;Yu,S.-Q.NewDrugsandClinicalRemendies1997,16(4),237(inChinese).　　(,,,新药与临床,1997,16(4),237.)19　Hui,X.-P.;Zhu,Y.NewDrugsandClinicalRemendies1997,16(6),355(inChinese).　　(,,新药与临床,1997,16(6),355.)20　Chen,R.-Y.;Chen,X.-R.Chem.J.Chin.Univ.1993,7,963(inChinese).　　(,,高等学校化学学报,1993,7,963.)21　Suzuki,M.;Matsumoto,T.;Mikami,T.;Suzuki,S.Chem.Pharm.Bull.1976,24,1100.22　Inoue,K.;Kawamoto,K.;Nakajima,H.;Kohno,M.;Kadoya,S.Carbohydr.Res.1983,115,199.23　Hu,M.;Hu,W.-W.;Xie,B.-J.Nat.Prod.Res.Dev.1990,2(2),8(inChinese).　　(,,,天然产物研究与开发,1990,2(2),8.)24　Williams,D.L.;Mcnamee,R.B.;Jones,E.L.;Pretus,H.A.;Ensley,H.E.;Browder,I.W.;DiLuzio,N.R.Carbohydr.Res.1991,219,203.25　Inoue,H.;Nakayama,H.;Tsuhako,M.Carbohydr.Res.2000,324(1),10.26　Tsuhako,M.;Sueyoshi,C.;Baba,Y.;Miyajima,T.;Ohashi,S.;Nariai,H.;Motooka,I.Chem.Lett.1987,1431.27　Inoue,H.;Baba,Y.;Tsuhako,M.Chem.Pharm.Bull.1995,43(4),677.28　Lee,S.;Lim,S.K.CerealChem.1998,75(5),690.29　Kim,K.B.;Beluman,E.J.CarbohydrRes.1995,270,71.(Y0111274　QIN,X.Q.)839No.11: