Glutamic acid, acyl derivatives

Other biocatalytic methods of producing D-p-hydroxyphenylglycine have not proved competitive, for instance transaminase based processes require glutamate to be supplied. Others include the hydrolysis of N-acyl derivatives by acylase and amides by aminopeptidase (DSM), the use of L-specrfic hydantoinases and immobilised subtilisin for the resolution of D,L-2-acetamido-/>-hydroxyphenylacetic acid methyl ester (Bayer). 

KOSiMe3 by a Beckmann-type rearrangement [39], and from glutamic acid derivatives by intramolecular acylation [40]. 

Addition of a-diazoketones derived from (W, A )-tartaric and (S )-glutamic acids, followed by dinitrogen extrusion, afforded enantiomerically pure 1,2-methano[60]fullerenes with an acylated methylene bridge.441 Bestmann and co-workers showed that these adducts can be thermally rearranged to substituted fullerene-fused dihydrofurans. 

C-Alkylation of the sodio derivative is accomplished by a technique similar to the alkylation of malonic ester. Primary halogen compounds, quaternary ammonium salts,and an alkene oxide have been used as alkylating agents. Alkylation by secondary halides has been less successful. Hydrolysis of the substituted esters to acetylated amino acids is described for leucine (64%) and phenylalanine (83%). Hydrolysis with deacylation has been used to prepare histidine (45%) and phenylalanine (67%). Glutamic acid (75%) is obtained from substituted acylaminomalonates prepared by the Michael condensation of methyl acrylate and the acylated amino esters. ... 

In the laboratory of D. Ma, the asymmetric synthesis of several metabotropic glutamate receptor antagonists derived from a-alkylated phenylglycines was undertaken. The preparation of (S)-1-aminoindan-1,5-dicarboxylic acid (AIDA) started with the Perkin reaction of 3-bromobenzaldehyde and malonic acid. The resulting ( )-cinnamic acid derivative was hydrogenated and the following intramolecular Friedel-Crafts acylation afforded the corresponding indanone, which was then converted to (S)-AIDA. 

Two D-aminoacylases have been described that resemble the L-specific acylase II from kidney, which only hydrolyzes the N-acyl derivatives of L-aspartic acid. The d-specific counterpart of acylase II, N-acetyl-D-aspartate deacetylase, has been isolated from Alcaligenes xylosoxydans subsp. xylosoxydans,n The same strain produces an aminoacylase which specifically hydrolyzes N-acyl derivatives of D-glutamic acid131L The latter N-acetyl-D-glutamate deacetylase has also been found in Pseudomonas sp. 33. ... 

Correspondingly, the use of other anhydrides of aliphatic acids provides the appropriate 2-acyl derivatives. Cyclization of glutamic acid dipeptides... 

The congeneric 0-acyl esters of iV-hydroxypyridine-2-selenone can also be prepared since the corresponding selenohydroxamic acid is readily available by treatment of 2-bromopyridine-iV-oxide with sodium borohydride and selenium. As shown in Scheme 11, this variant of the decarboxylative rearrangement, when followed by ozonolysis and subsequent selenoxide elimination, provided a useful route to optically pure L-vinylglycine from a protected glutamic acid derivative [16]. 

Synonyms Glutamic acid, N-coco acyl derive. 

Uses Surfactant in cosmetics Disodium cocoyl glutamate CAS 68187-30-4 EINECS/ELINCS 269-085-1 Synonyms L-Glutamic acid, N-coco acyl derive., disodium salt... 

Disodium hydrogenated tallow glutamate CAS 38079-62-8 EINECS/ELINCS 253-773-7 Synonyms Glutamic acid, N-tallow-acyl derivs.. 

Glutamic acid, N-coco acyl derivs.. SeeCocoyl glutamic acid... 

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