2-amino-2-methylsuccinic acid

Names

[ Name ]:
2-amino-2-methylsuccinic acid

[Synonym ]:
2-Amino-2-methylsuccinic acid
D-Aspartic acid,2-methyl-,hydrochloride (1:1)
2-Methylaspartic acid
MFCD00056709
Aspartic acid,2-methyl
2-Amino-2-methyl-bernsteinsaeure

Biological Activity

[Description]:

α-Methyl-DL-aspartic acid is a specific inhibitor of argininosuccinate synthase (ASS), and also is the rate-limiting enzyme for the recycling of 1-citrulline to 1-arginine[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

α-methyl-dl-aspartic acid can significantly reduce the anti-hypertensive activity of Bj-BPP-10c in SHR[2].

[In Vivo]

α-methyl-dl-aspartic acid (147 mg/kg, i.v.) can diminish the l-citrulline-induced retinal vasodilation in Wistar rats[1]. Animal Model: Wistar rats Dosage: 147 mg/kg Administration: 147 mg/kg, i.v. Result: Attenuated the increase of retinal arteriolar diameter induced by L-citrulline.

[References]

[1]. Asami Mori, et al. l-Citrulline dilates rat retinal arterioles via nitric oxide- and prostaglandin-dependent pathways in vivo. J Pharmacol Sci. 2015 Apr;127(4):419-23.

[2]. Juliano R Guerreiro, et al. Argininosuccinate synthetase is a functional target for a snake venom anti-hypertensive peptide: role in arginine and nitric oxide production. J Biol Chem. 2009 Jul 24;284(30):20022-33.

Chemical & Physical Properties

[ Melting Point ]:
232-234ºC

[ Molecular Formula ]:
C₅H₉NO₄

[ Molecular Weight ]:
147.12900

[ Exact Mass ]:
147.05300

[ PSA ]:
100.62000

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2922499990

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922499990

[ Summary ]:
HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

Articles

Binding of C5-dicarboxylic substrate to aspartate aminotransferase: implications for the conformational change at the transaldimination step.

Biochemistry 44(23) , 8218-29, (2005)

The mechanism for the reaction of aspartate aminotransferase with the C4 substrate, l-aspartate, has been well established. The binding of the C4 substrate induces conformational change in the enzyme ...

Endothelial nitric oxide production is tightly coupled to the citrulline-NO cycle.

Nitric Oxide 17 , 115-121, (2007)

Nitric oxide (NO) is an important vasorelaxant produced along with L-citrulline from L-arginine in a reaction catalyzed by endothelial nitric oxide synthase (eNOS). Previous studies suggested that the...

Crystal structures of Escherichia coli aspartate aminotransferase in two conformations. Comparison of an unliganded open and two liganded closed forms.

J. Mol. Biol. 239(2) , 285-305, (1994)

Three crystal structures of wild type E. coli aspartate aminotransferase (E.C.2.6.1.1) in space group P2(1) have been determined at resolution limits between 2.6 and 2.35 A. The unliganded enzyme and ...