53759-36-7

Basic information

• Product Name: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester
• Synonyms: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester;γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate;(R)-5-(benzyloxy)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-5-oxopentanoic acid;Boc-Ala-D-Glu(OBzl)-OH
• CAS NO: 53759-36-7
• Molecular Formula: C₂₀H₂₈N₂O₇
• Molecular Weight: 408.44552
• Mol File: 53759-36-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester(53759-36-7)
• EPA Substance Registry System: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester(53759-36-7)

Safety Data

• Hazardous Substances Data: 53759-36-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester is used as a research tool for exploring its potential therapeutic benefits, given its unique structural features and the possibility of it being a precursor to new drug candidates.
Used in Drug Delivery Systems:
In the field of drug delivery, N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester is utilized as a component in the design of innovative systems aimed at improving the efficacy and targeting of pharmaceutical agents, potentially enhancing their bioavailability and therapeutic outcomes.
Used in the Design and Synthesis of Novel Pharmacological Agents:
N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-D-glutamic acid 5-(phenylmethyl) ester serves as a key building block in the synthesis of new pharmacological agents, leveraging its unique chemical properties to create compounds with specific biological activities and potential applications in medicine.
Used in Investigating New Drug Candidates:
This peptide derivative is employed in the investigation of new drug candidates, where its specific properties and potential biological activities are explored to identify and develop novel therapeutic agents with improved pharmacological profiles.

Upstream product

• 100-51-6 benzyl alcohol 
• 6893-26-1 D-Glutamic acid 
• 15761-38-3 L-N-Boc-Ala 
• 2578-33-8 D-glutamic acid-5-benzyl ester 
• 3392-05-0 Boc-Ala-O-N-hydroxysuccinimide 

Downstream Products

• 143673-80-7 α-octadecylamide of γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate 
• 1570068-97-1 Boc-Ala-^DGlu(Bzl)-Phe-CONHCH₂COCH₃ 
• 1570068-68-6 Boc-Ala-^DGlu(OBzl)-Phe-CO₂CH₂COCH₃ 
• 65671-47-8 C₂₁H₃₀N₂O₇ 
• 18814-49-8 tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester 

Relevant articles and documents

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.

BIOHYBRID PEPTIDOGLYCAN OLIGOMERS

The invention relates to a compound of formula la and/or formula lb: or a pharmaceutically acceptable salt, solvate or prodrug thereof, where the groups are defined herein. The invention also relates to a pharmaceutical formulation comprising the compound

Transpeptidase-mediated incorporation of d-amino acids into bacterial peptidoglycan

The β-lactams are the most important class of antibiotics in clinical use. Their lethal targets are the transpeptidase domains of penicillin binding proteins (PBPs), which catalyze the cross-linking of bacterial peptidoglycan (PG) during cell wall synthesis. The transpeptidation reaction occurs in two steps, the first being formation of a covalent enzyme intermediate and the second involving attack of an amine on this intermediate. Here we use defined PG substrates to dissect the individual steps catalyzed by a purified E. coli transpeptidase. We demonstrate that this transpeptidase accepts a set of structurally diverse d-amino acid substrates and incorporates them into PG fragments. These results provide new information on donor and acceptor requirements as well as a mechanistic basis for previous observations that noncanonical d-amino acids can be introduced into the bacterial cell wall.

Synthesis of γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate and its derivatives

A convenient method of obtaining Boc-L-Ala-D-iGln-OBzl and its amide analogs by condensing the N-hydroxysuccinimidyl ester of Boc-L-Ala with the γ-benzyl ester of D-Glu in the presence of NaHCO3, followed by amidation of the resulting Boc-L-Ala-D-Glu-γ-OBzl, is proposed. The use of l-adamantylamine and octadecylamine as amino components has enabled the corresponding α-adamantylamide and octadecylamide of the dipeptide to be obtained.

Transformations of glycyrrhizic acid. XIII. Synthesis of peptide derivatives of monomethyl glycyrrhizate

Novel dipeptide derivatives of glycyrrhizic acid monomethyl ester were synthesized by its condensation with Ala-Glu (or D-Glu) derivatives using Woodward K reagent or the active ester method. Two of the compounds prepared stimulated delayed hypersensitivi

Immunizing and anti-infectious adjuvant agents constituted by N-acetyl-muramyl-L-alanyl-D-glutamic acid derivatives

The invention relates to new water-soluble agents which are effective as immunizing adjuvants. These adjuvant agents are the methyl, ethyl or propyl esters of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-isoglutamine and of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid, the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-(α-methylamide)-glutamic and 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-isoglutamine, the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-glutamic acid and their derivatives. They are particularly useful to prepare adjuvant medicinal compositions, used for increasing the efficiency of vaccines.