A NEW METHOD FOR THE SYNTHESIS OF N-EPSILON-ACETYL-N-EPSILON-HYDROXY-L-LYSINE, THE IRON-BINDING CONSTITUENT OF SEVERAL IMPORTANT SIDEROPHORES

被引:34
作者
HU, JD [1 ]
MILLER, MJ [1 ]
机构
[1] UNIV NOTRE DAME, DEPT CHEM & BIOCHEM, NOTRE DAME, IN 46556 USA
关键词
D O I
10.1021/jo00096a030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidation of the <epsilon)-amino group of N(a)lpha-(carbobenzyloxy)-L-lysine methyl ester with dimethyldioxirane in acetone gave the acetone-derived nitrone of the desired hydroxylamine. Acidic hydrolysis, acetylation, and subsequent deprotection provided a short synthesis of N-epsilon-acetyl-N-epsilon-hydroxy-L-lysine, the iron-binding constituent of important microbial siderophores.
引用
收藏
页码:4858 / 4861
页数:4
相关论文
共 32 条
[1]   SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].
ADAM, W ;
CHAN, YY ;
CREMER, D ;
GAUSS, J ;
SCHEUTZOW, D ;
SCHINDLER, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803
[2]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[3]   ALBOMYCINS .2. ABSOLUTE-CONFIGURATION OF THE DEFERRI FORM OF THE ALBOMYCINS [J].
BENZ, G ;
BORN, L ;
BRIEDEN, M ;
GROSSER, R ;
KURZ, J ;
PAULSEN, H ;
SINNWELL, V ;
WEBER, B .
LIEBIGS ANNALEN DER CHEMIE, 1984, (08) :1408-1423
[4]   THE TOTAL SYNTHESIS OF NANNOCHELIN - A NOVEL CINNAMOYL HYDROXAMATE-CONTAINING SIDEROPHORE [J].
BERGERON, RJ ;
PHANSTIEL, O .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7140-7143
[5]   SYNTHETIC STUDIES RELATED TO MYCOBACTINS .2. FORMATION OF MYCOBACTIN HYDROXAMIC ACID UNITS BY MALONIC ESTER SYNTHESIS [J].
BLACK, DSC ;
BROWN, RFC ;
WADE, AM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (10) :2155-&
[6]   IMINES AND DERIVATIVES .24. NITRONE SYNTHESIS BY IMINE OXIDATION USING EITHER A PEROXYACID OR DIMETHYLDIOXIRANE [J].
BOYD, DR ;
COULTER, PB ;
MCGUCKIN, MR ;
SHARMA, ND ;
JENNINGS, WB ;
WILSON, VE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :301-306
[7]   DIMETHYLDIOXIRANE OXIDATION OF PRIMARY AMINES [J].
CRANDALL, JK ;
REIX, T .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6759-6764
[8]  
HAEHR H, 1971, PURE APPL CHEM, V28, P603
[9]   A SYNTHESIS OF (+/-)-BREFELDIN-A [J].
HONDA, M ;
HIRATA, K ;
SUEOKA, H ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1981, 22 (28) :2679-2682
[10]  
JACKSON AE, 1976, SYNTHESIS-STUTTGART, P685