NOVEL QUATERNARY AMMONIUM SALT-CONTAINING POLYAMINES FROM THE AGELENOPSIS-APERTA FUNNEL-WEB SPIDER

被引:43
作者
JASYS, VJ [1 ]
KELBAUGH, PR [1 ]
NASON, DM [1 ]
PHILLIPS, D [1 ]
ROSNACK, KJ [1 ]
FORMAN, JT [1 ]
SACCOMANO, NA [1 ]
STROH, JG [1 ]
VOLKMANN, RA [1 ]
机构
[1] PFIZER INC,DIV CENT RES,GROTON,CT 06340
关键词
D O I
10.1021/jo00032a039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel hydroxylamine-containing acylpolyamines, Agel 489a and Agel 505a, each bearing a terminal quaternary ammonium salt, were isolated from the venom of Agelenopsis aperta, a funnel-web spider found throughout the western United States. Published structures for these compounds were not consistent with our spectral data. On the basis of fast-atom bombardment (FAB) mass spectrometry and H-1 and C-13 NMR spectra, novel structures for Agel 489a and 505a are proposed. These structural assignments are confirmed by the total synthesis of Agel 489a.
引用
收藏
页码:1814 / 1820
页数:7
相关论文
共 14 条
[1]   2 CLASSES OF CHANNEL-SPECIFIC TOXINS FROM FUNNEL WEB SPIDER VENOM [J].
ADAMS, ME ;
HEROLD, EE ;
VENEMA, VJ .
JOURNAL OF COMPARATIVE PHYSIOLOGY A-SENSORY NEURAL AND BEHAVIORAL PHYSIOLOGY, 1989, 164 (03) :333-342
[2]   POTASSIUM FLUORIDE ON CELITE - VERSATILE REAGENT FOR C-ALKYLATION,N-ALKYLATION,O-ALKYLATION, AND S-ALKYLATION [J].
ANDO, T ;
YAMAWAKI, J .
CHEMISTRY LETTERS, 1979, (01) :45-46
[3]   AN ELECTRIC METHOD TO OBTAIN LOXOSCELES SPIDER VENOM [J].
BASCUR, L ;
YEVENES, I ;
ADRIAN, H .
TOXICON, 1980, 18 (02) :224-224
[4]  
HOUSSIN R, 1988, SYNTHESIS-STUTTGART, P259
[5]   ISOLATION, STRUCTURE ELUCIDATION, AND SYNTHESIS OF NOVEL HYDROXYLAMINE-CONTAINING POLYAMINES FROM THE VENOM OF THE AGELENOPSIS-APERTA SPIDER [J].
JASYS, VJ ;
KELBAUGH, PR ;
NASON, DM ;
PHILLIPS, D ;
ROSNACK, KJ ;
SACCOMANO, NA ;
STROH, JG ;
VOLKMANN, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6696-6704
[6]   THE TOTAL SYNTHESIS OF ARGIOTOXIN-636, ARGIOTOXIN-659 AND ARGIOTOXIN-673 [J].
JASYS, VJ ;
KELBAUGH, PR ;
NASON, DM ;
PHILLIPS, D ;
SACCOMANO, NA ;
VOLKMANN, RA .
TETRAHEDRON LETTERS, 1988, 29 (48) :6223-6226
[7]  
JUST G, 1976, SYNTHESIS-STUTTGART, P457
[8]   SYNTHESIS OF NEUROTOXIC NEPHILA SPIDER VENOMS - NSTX-3 AND JS']JSTX-3 [J].
NASON, DM ;
JASYS, VJ ;
KELBAUGH, PR ;
PHILLIPS, D ;
SACCOMANO, NA ;
VOLKMANN, RA .
TETRAHEDRON LETTERS, 1989, 30 (18) :2337-2340
[9]  
PARKS TN, 1991, J BIOL CHEM, V266, P21523
[10]   STRUCTURES OF PARALYTIC ACYLPOLYAMINES FROM THE SPIDER AGELENOPSIS-APERTA [J].
QUISTAD, GB ;
SUWANRUMPHA, S ;
JAREMA, MA ;
SHAPIRO, MJ ;
SKINNER, WS ;
JAMIESON, GC ;
LUI, A ;
FU, EW .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 169 (01) :51-56