TOTAL SYNTHESIS OF NODRM(IV) (S) - A SULFATED LIPOTETRASACCHARIDE SYMBIOTIC SIGNAL FROM RHIZOBIUM-MELILOTI

被引:33
作者
TAILLER, D [1 ]
JACQUINET, JC [1 ]
BEAU, JM [1 ]
机构
[1] UNIV ORLEANS,BIOCHIM STRUCT LAB,F-45067 ORLEANS,FRANCE
关键词
D O I
10.1039/c39940001827
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereocontrolled synthesis of the sodium salt of NodRm(IV) (S), the bacterial chemical signal involved in the Rhizobium meliloti-alfalfa symbiosis, has been achieved in an overall yield of 8%.
引用
收藏
页码:1827 / 1828
页数:2
相关论文
共 22 条
[1]   A FAST PROCEDURE FOR THE REDUCTION OF AZIDES AND NITRO-COMPOUNDS BASED ON THE REDUCING ABILITY OF SN(SR)3-SPECIES [J].
BARTRA, M ;
ROMEA, P ;
URPI, F ;
VILARRASA, J .
TETRAHEDRON, 1990, 46 (02) :587-594
[2]   VERSATILE BEHAVIOR OF O-STANNYLATED D-GLUCAL TOWARDS HALOGENS [J].
CZERNECKI, S ;
LETEUX, C ;
VEYRIERES, A .
TETRAHEDRON LETTERS, 1992, 33 (02) :221-224
[3]  
DENARIE J, 1992, MOL SIGNALS PLANT MI, P295
[4]   RHIZOBIUM - PLANT SIGNAL EXCHANGE [J].
FISHER, RF ;
LONG, SR .
NATURE, 1992, 357 (6380) :655-660
[5]  
HELFERICH B, 1959, CHEM BER, V86, P604
[6]  
Lemieux R. U., 1976, ACS SYM SER, V39, P90, DOI DOI 10.1021/BK-1977-0039.CH006
[7]   SYMBIOTIC HOST-SPECIFICITY OF RHIZOBIUM-MELILOTI IS DETERMINED BY A SULFATED AND ACYLATED GLUCOSAMINE OLIGOSACCHARIDE SIGNAL [J].
LEROUGE, P ;
ROCHE, P ;
FAUCHER, C ;
MAILLET, F ;
TRUCHET, G ;
PROME, JC ;
DENARIE, J .
NATURE, 1990, 344 (6268) :781-784
[8]   TOTAL SYNTHESIS OF THE NODRM-IV FACTORS, THE RHIZOBIUM NODULATION SIGNALS [J].
NICOLAOU, KC ;
BOCKOVICH, NJ ;
CARCANAGUE, DR ;
HUMMEL, CW ;
EVEN, LF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) :8701-8702
[9]   BUILDING UNITS FOR OLIGOSACCHARIDES .10. SYNTHESIS OF ALPHA-1-]4 AND ALPHA-1-]3 LINKED DISACCHARIDES OF 2-AMINO-2-DEOXY-D-GLUCOPYRANOSE BY AZIDE METHOD [J].
PAULSEN, H ;
STENZEL, W .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (06) :2348-2357
[10]   BUILDING UNITS FOR OLIGOSACCHARIDES .9. STEREOSELECTIVE SYNTHESIS OF ALPHA-GLYCOSIDICALLY LINKED DISACCHARIDES AND OLIGOSACCHARIDES OF 2-AMINO-2-DEOXY-D-GLUCOPYRANOSE [J].
PAULSEN, H ;
STENZEL, W .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (06) :2334-2347