Efficient method for the preparation of (S)-5-hydroxynorvaline

Characterization of the Polyoxin Biosynthetic Gene Cluster from Streptomyces cacaoi and Engineered Production of Polyoxin H

“…Synthesis of AHV-Synthesis of AHV was according to method of Garcia et al (27). The synthesized AHV was confirmed by 1…”

Accumulation of 5-hydroxynorvaline in maize (Zea mays) leaves is induced by insect feeding and abiotic stress

“…Together, these NMR and MS spectra showed that the identified maize metabolite was 5-hydroxynorvaline. Since 5-hydroxynorvaline is not commercially available, the authentic compound was synthesized from l -glutamate, as described previously ( Garcia et al , 2000 ; Supplementary Fig. 2 ).…”

“…In order to confirm the structure of the maize metabolite, authentic l - 5-hydroxynorvaline was synthesized from l -glutamic acid as described previously ( Garcia et al , 2000 ). The reaction mixture was passed through a Dowex 50WX8-200 column, eluted with 80% acetonitrile and collected in tubes as 3ml fractions.…”

A Convenient Reduction of α-Amino Acids to 1,2-Amino Alcohols With Retention of Optical Purity~!2008-08-29~!2008-10-16~!2008-11-28~!

“…The conversion of -amino acids into 1,2-amino alcohols provides access to a pool of useful chiral intermediates. Numerous methods have been developed for the reduction of unprotected [1][2][3][4][5][6][7][8][9][10] 1 or N-protected [4,5,[11][12][13][14][15][16][17][18][19][20][21][22][23][24] 2 -amino acids to the corresponding amino alcohols, including procedures in which the acid group is activated by conversion to a mixed anhydride [11][12][13][14][15], acid fluoride [18] or active ester [16,[20][21][22][23], followed by reduction with sodium borohydride. We required a number of amino alcohols as intermediates for peptidomimetic synthesis, but found the standard mixed anhydride method to be capricious in our hands.…”