3- aminoglutarates

Hatanaka and co-workers found that carbapenem derivatives were readily available by means of an Ugi-4CR between 3-aminoglutaric acid mono-t-butyl ester, formaldehyde, and 4-nitrobenzyl isocyanide that gave the /l-lactam 156, which was converted into the 4-nitrobenzyl ester 157. The subsequent stereoselective Dieckmann condensation allowed the preparation of the 2-oxocarbapenem derivative 158 (Scheme 2.57) [87]. 

By a mixture of chemical and enzymatic methods, Japanese workers have succeeded in preparing (5)- and (/ )-4-methoxycarbonylmethylazetidin-2-one (12) and (11). As shown in Scheme 3, treatment of dimethyl (3-aminoglutarate... 

A -formyl group. Subsequently, dl-(VIII.64) was prepared by a modified Taylor synthesis by Rosowsky et al. [265], 4-(7V-Methyl-A -tosylamino)benzoyl chloride was condensed with diethyl DL-3-aminoglutarate, the tosyl group was removed with HBr, the resultant amine was coupled to 2-amino-5-chlorome-thyl-3-cyanopyrazine A -oxide [24], and the 7V-oxide was directly reduced to amino nitrile dl-(VIII.66) with triethyl phosphite and condensed with guanidine carbonate to form diester dl-(VIII.64) in low yield. 

There are several methods to improve reactivities and selectivities of enzymatic reactions in case they are not sufficient for practical use. Modification of substrate structure and reaction conditions as well as screening and genetic modification of enzymes can improve reactions. For example, although hydrolysis of dimethyl/3-aminoglutarate by pig liver esterase afforded the (P)-monoester in 40% ee, modification of the amino moiety with a benzyloxycarbonyl group reversed the stereoselectivity and afforded the (S)-monoester in >96% ee and 93% chemical yield (Fig. 10.24(a) In the lipase-catalyzed hydrolysis of cyano acetate, a method... 

S)-15-Aminoethyl-14-hydroxy-5,5-dimethyl-2,8-dithia[9](2,5)pyridinophanc, 29-30 0-Aminoglutarate, 265 Aminomcrcuration, 315 a-Aminomethyl ketones, 274, 352-353... 

To date, the composition of active sites is known for many enzymes, the most probable action mechanisms are suggested, and comparison data exist on catalytic group properties in enzymes and free molecules in solutions. Note also that the chemical composition of catalytic active sites of enzymes is independent of the presence of any specific compounds. Moreover, the majority of them are the well-known compounds for homogeneous catalysis histidine imidazole, carboxylic groups of aspartic and aminoglutaric acids, flavins, hemins, etc. However, as homogeneous catalysts, they possess rather moderate or even poor catalytic activity in appropriate reactions. 

Aspartic acid, aminosuccinic acid, HOOC.CH2.CHNH2.COOH. Glutamic acid, a-aminoglutaric acid, HOOC.CH2.CH2.CHNH2.COOH. Diamino-monocarboxylic Acids. 

Glutamic acid, (Glu, E), a-aminoglutaric acid, H00C-CH2CH2CH(NH2)-C00H, C5H9NO4, Mr 147.13 Da, a proteinogenic amino acid. 

Synonyms cas bs-is-s a-AMiNooLUTARic acid hydrochloride /-2-aminoglutaric acid hydrochloride 2-... 

Aminoglutaramidic acid. See L-Glutamine o-Aminoglutaric acid L-2-Aminoglutaric acid. 

L-2-Aminoglutaric acid hydrochloride. See L-Glutamic acid hydrochloride... 

CAS 56-86-0 EINECS/ELINCS 200-293-7 FEMA 3285 INS620 E620 Synonyms a-Aminoglutaric acid L-2-Aminoglutaric acid 2-Aminopentanedioic acid L-2-Aminopentanedioic acid 1-Ami nopropane-1,3-dicarboxylic acid... 

L-Glutamic acid, N-hexadecanoyl-. See Palmitoyl glutamic acid L-Glutamic acid hydrochloride CAS 138-15-8 EINECS/ELINCS 205-315-9 Synonyms L-2-Aminoglutaric acid hydrochloride 2-Aminopentanedioic acid hydrochloride Empirical C6H9NO4 CIH Formula HOOCCH2CH2CH(NH2)COOH HCI Properties Orthorhombic bisphenoidal plates m.w. 183.60 dec. 214 C... 

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