57584-59-5

Basic information

• Product Name: L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester
• CAS NO: 57584-59-5
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.282
• Mol File: 57584-59-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester(57584-59-5)
• EPA Substance Registry System: L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester(57584-59-5)

Safety Data

• Hazardous Substances Data: 57584-59-5(Hazardous Substances Data)

Usage

Description

L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester, also known as Glu(OBzl)-OMe, is an organic compound derived from L-glutamic acid, an essential amino acid. It is characterized by the presence of a benzyl ester group (OBzl) and a methyl ester group (OMe) attached to the carboxylic acid and amino groups, respectively. L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester is known for its potential applications in various fields due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester is used as a reagent for the synthesis of cyclic tripeptides. These tripeptides have the potential to act as inhibitors for HMG-CoA reductase, an enzyme that plays a crucial role in cholesterol synthesis. By inhibiting this enzyme, these cyclic tripeptides can help in the treatment of cardiovascular diseases, making Glu(OBzl)-OMe a valuable compound in the development of new therapeutic agents.
Used in Polymer Industry:
L-Glutamic acid, 1-methyl 5-(phenylmethyl) ester is also used as a reagent in the preparation of bis(lactams), which are important building blocks for the synthesis of polymers. These polymers have potential applications in the development of organic solar cells, a rapidly growing field in the renewable energy sector. The use of Glu(OBzl)-OMe in the synthesis of these polymers contributes to the advancement of sustainable energy solutions and the development of more efficient solar cell technologies.

Upstream product

• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 67-56-1 methanol 
• 100-51-6 benzyl alcohol 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 59279-58-2 N^α-tert-butyloxycarbonyl-γ-benzyloxycarbonyl-L-glutamic acid methyl ester 

Downstream Products

• 1053423-71-4 -L-glutamic acid 1-methyl 5-benzyl diester 
• 216309-95-4 -L-glutamic acid 1-methyl 5-benzyl diester 
• 65671-47-8 (S)-5-benzyl 1-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pentanedioate 

Relevant articles and documents

Carboxylic Anhydride Synthesis from γ-Benzyl-L-glutamate and Dimethyl Carbonate

A green, environmentally friendly, and nontoxic method was developed to synthesize carboxylic anhydrides (NCAs) from γ-benzyl-l-glutamate (BLG) and dimethyl carbonate (DMC) though two steps: synthesis of N-methoxycarbonyl-γ-benzyl-l-glutamate intermediate (NOM-BLG) and cyclization. The highest yields of NOM-BLG (up to 83.7%) and NCA-BLG (up to 66.7%) were obtained. Most importantly, the use of DMC will open an innovative door to synthesize NCAs.

Studies on selectin blockers. 7. Structure-activity relationships of sialyl Lewis X mimetics based on modified ser-glu dipeptides

We have previously found that heterochiral fucodipeptides, L-Ser-D-Glu (3a) and D-Ser-L-Glu (3b), exhibited up to 20-100 times more potency than a sialyl Lewis X (sLe(X), 1) and a 3'sulfated Lewis X analogue (2) toward E- selectin binding and have also proposed, from molecular dynamics calculation, that their strong activities would depend on a possible formation of the type II and/or type II' β-turn of compounds 3a,b (Tsukida, T.; Hiramatsu, Y.; Tsujishita, H.; Kiyoi, T.; Yoshida, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534-3541). To clarify our hypothesis, we synthesized several analogues of compounds 3a,b and investigated their structure-activity relationships. As a result, it was indicated that the type II and/or type II' β-turn conformation would be a comparatively tight form and would play important roles in favorable binding to E-selectin. These findings indicate that sLe(X) mimetics with type II and type II' β-turn dipeptides could be a useful methodology for the design of an active selectin blocker.