1,1'-ETHYLIDENEBIS(L-TRYPTOPHAN), STRUCTURE DETERMINATION OF CONTAMINANT-97 - IMPLICATED IN THE EOSINOPHILIA-MYALGIA-SYNDROME (EMS)

被引:56
作者
SMITH, MJ
MAZZOLA, EP
FARRELL, TJ
SPHON, JA
PAGE, SW
ASHLEY, D
SIRIMANNE, SR
HILL, RH
NEEDHAM, LL
机构
[1] US FDA, CTR FOOD SAFETY & APPL NUTR, FOOD FORMULAT BRANCH, WASHINGTON, DC 20204 USA
[2] CTR DIS CONTROL, CTR ENVIRONM HLTH & INJURY CONTROL, TOXICOL BRANCH, ATLANTA, GA 30333 USA
关键词
D O I
10.1016/S0040-4039(00)74469-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The condensation of tryptophan and acetaldehyde affords a bisindolylaminal of tryptophan which is indistinguishable from contaminant "97". The formation and decomposition of aminals is addressed in light of epidemiological evidence linking them to a recent outbreak of EMS.
引用
收藏
页码:991 / 994
页数:4
相关论文
共 19 条
[1]   AN INVESTIGATION OF THE CAUSE OF THE EOSINOPHILIA-MYALGIA SYNDROME ASSOCIATED WITH TRYPTOPHAN USE [J].
BELONGIA, EA ;
HEDBERG, CW ;
GLEICH, GJ ;
WHITE, KE ;
MAYENO, AN ;
LOEGERING, DA ;
DUNNETTE, SL ;
PIRIE, PL ;
MACDONALD, KL ;
OSTERHOLM, MT .
NEW ENGLAND JOURNAL OF MEDICINE, 1990, 323 (06) :357-365
[2]  
DUBIN DT, 1960, J BIOL CHEM, V235, P783
[3]  
DUHAMEL L, 1982, CHEM AMINO NITROSO N, V2, P849
[4]  
HAYNES LW, 1969, ENAMINES SYNTHESIS S, P55
[5]   1-FLUORO-2,4-DINITROBENZENE AS A QUANTITATIVE REAGENT FOR PRIMARY AND SECONDARY AMINES [J].
MCINTIRE, FC ;
CLEMENTS, LM ;
SPROULL, M .
ANALYTICAL CHEMISTRY, 1953, 25 (11) :1757-1758
[6]   ELECTROPHILIC SUBSTITUTION IN SKATOLE AND ITS DERIVATIVES [J].
NOLAND, WE ;
ROBINSON, DN .
TETRAHEDRON, 1958, 3 (01) :68-72
[7]  
PITACCO G, 1982, CHEM AMINO NITROSO N, V1, P623
[8]   PREPARATION AND PROPERTIES OF 2,4-DINITROPHENYL-L-AMINO ACIDS [J].
RAO, KR ;
SOBER, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) :1328-1331
[9]   MECHANISM OF REACTION OF PHTHALALDEHYDIC ACID WITH INDOLES . INTRAMOLECULAR CATALYSIS IN ALDEHYDE REACTIONS [J].
REES, CW ;
SABET, CR .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :680-&
[10]  
REMERS WA, 1972, INDOLES, V1, P1