N-Hydroxyaspartic acid

No practical chemical synthesis of dl- or L-N-hydroxyaspartic acid has been described. 

Emery, T. Aspartase catalyzed synthesis of N-hydroxyaspartic acid. Biochemistry 2, 1041 (1963). 

Addition of hydroxylamine to the double bond of fumaric acid was accelerated by aspartase but unstable N-hydroxyaspartic acid was not isolated (57,154). 

Kolasa, T. Synthetic Study of N-Hydroxyaspartic Acid. Canad. J. Chem. 65, 2139 (1985). 

Alterobactin, a 19-membered macrocydic depsipeptide containing two types of unusual building block, two i-threo- -hydroxyaspartic acids and one (3S,4S)-4,8-diamino-3-hydroxyoctanic acid attached to a catechol carboxylate at the N -site. It was isolated from a open-ocean bacterium M-teromonas luteoviolacea coUected off Chub Cay, Bahamas. Alterobadin is a depsipeptide siderophore exhibiting extraordinary affinity for ferric ion. The total synthesis has been described [R. T. Reid et al.. Nature 1993, 366, 455 J. Deng et al.. Synthesis 1998, 627]. 

Asymmetric aldol reactions of a-keto esters (R-CO-COOMe R = Me, iBu, Ph) with methyl isocyanoacetate or N,N-dimethyl-a-isocyanoacetamide in the presence of 1 mol% of a chiral ferrocenylphosphine-gold(I) catalyst proceed enantiose-lectively (up to 90% cc) to give the corresponding oxazolines, which can be converted into optically active j8-alkyl-j8-hydroxyaspartic acid derivatives [1197]. Dehydration of the intermediate formamide to the corresponding isocyanide is accomplished in 97% yield with phosphoryl chloride at room temperature within 2h. 

Amino-acid analogs and uncommon L-amino acids W-acetyl-aspartate, W-acetyl-serine, oi-amino-n-butyrate, 3-aminoisobutyrate, aspartate ethyl or methyl ester, citrulline, cysteate, fumarate, glutathione, homoserine, erythro- and threo-p-hydroxyaspartate, isoasparagine, isoserine, malate, a- and p-methylaspartate, methylserine, phenol, serine amide, serine methyl ester, succinate [498, 747]... 

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