PHOSPHORYLATED SUGARS .26. SYNTHESIS OF 3-DEOXY-D-MANNO-OCT-2-ULOSONIC ACID 7-PHOSPHATE

被引：2

作者：

AUZANNEAU, FI ^{[1
]}

CHARON, D ^{[1
]}

SZABO, L ^{[1
]}

机构：

[1] UNIV PARIS 11,CTR ETUDES PHARMACEUT,CNRS,EQUIPE ENDOTOXINES,URA 1116,F-92290 CHATENAY MALABRY,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 10期

关键词：

D O I：

10.1039/p19900002831

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Of several phosphorylation methods tried, only that with bis(trichloroethyl) phosphorochloridate was satisfactory in producing the title compound starting either from methyl (methyl 8-O-benzyl-3-deoxy-4,5-O- isopropylidene-α-D-manno-oct-2-ulopyranosid)onate or from methyl 4,8-di-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosidono-1,5-lactone. The synthesis of the phosphodiester methyl (methyl 3-deoxy-α-D-manno-oct-2- ulopyranosid)onate 7-(acetamidoethyl ammonium phosphate) is also described.

引用

收藏

页码：2831 / 2834

页数：4

相关论文

共 22 条

[1] CHEMISTRY OF BACTERIAL-ENDOTOXINS .5. SYNTHESIS OF 1,5-LACTONES OF 3-DEOXY-D-MANNO-2-OCTULOPYRANOSONIC ACID (KDO) [J].

AUZANNEAU, FI ;

CHARON, D ;

SZABO, L ;

MERIENNE, C .

CARBOHYDRATE RESEARCH, 1988, 179 :125-136

[2] STRUCTURAL ELUCIDATION OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID CONTAINING MENINGOCOCCAL 29-E CAPSULAR POLYSACCHARIDE ANTIGEN USING C-13 NUCLEAR MAGNETIC-RESONANCE [J].

BHATTACHARJEE, AK ;

JENNINGS, HJ ;

KENNY, CP .

BIOCHEMISTRY, 1978, 17 (04) :645-651

[3] OCCURRENCE OF 2-KETO-DEOXYOCTONIC ACID 5-PHOSPHATE IN LIPOPOLYSACCHARIDES OF VIBRIO-CHOLERAE OGAWA AND INABA [J].

BRADE, H .

JOURNAL OF BACTERIOLOGY, 1985, 161 (02) :795-798

[4] HYDROLYSIS OF ESTERS OF MONORIBONUCLEOTIDES [J].

BROWN, DM ;

MAGRATH, DI ;

NEILSON, AH ;

TODD, AR .

NATURE, 1956, 177 (4520) :1124-1125

[5] NUCLEOTIDES .34. THE HYDROLYSIS OF DIALKYL ESTERS OF URIDINE-3' PHOSPHATE AND ITS RELEVANCE TO THE QUESTION OF PHOSPHOTRIESTER LINKAGES IN RIBONUCLEIC ACIDS [J].

BROWN, DM ;

MAGRATH, DI ;

TODD, AR .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :4396-4401

[6] DETECTION OF 3-DEOXY-2-OCTULOSONIC ACID IN THIOBARBITURATE-NEGATIVE ENDOTOXINS [J].

CAROF, M ;

LEBBAR, S ;

SZABO, L .

CARBOHYDRATE RESEARCH, 1987, 161 (01) :C4-C7

[7] DO ENDOTOXINS DEVOID OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID EXIST [J].

CAROFF, M ;

LEBBAR, S ;

SZABO, L .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 143 (03) :845-847

[8] 3-DEOXY-2-OCTULOSONIC ACID 5-PHOSPHATE - COMPONENT OF ENDOTOXIN OF BORDETELLA-PERTUSSIS [J].

CHABY, R ;

SZABO, L .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1975, 59 (01) :277-280

[9] PHOSPHORYLATED SUGARS .20. SYNTHESIS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID 8-(DIHYDROGEN PHOSPHATE) [J].

CHARON, D ;

SZABO, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (15) :1628-1632

[10] PYRANOSIDE DERIVATIVES OF 3-DEOXYALD-2-ULOSONIC ACIDS [J].

CHARON, D ;

SZABO, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1971-1977