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Usage

Uses

Used in Pharmaceutical Industry:
(RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid is used as a protective group for serine in the synthesis of complex organic molecules and peptides. It is crucial for the development of new drugs and biologically active compounds, ensuring the stability and reactivity of the serine molecule during the synthesis process.
Used in Biotechnology Industry:
In the biotechnology field, (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid is employed as a protective agent for serine during the synthesis of bioactive peptides and proteins. (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid aids in the development of novel therapeutic agents and the study of protein structure and function.
Used in Material Science:
(RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid is also utilized in the development of new materials, where its protective properties for serine can be harnessed to create innovative compounds with specific properties and applications.
Used in Protein Structure and Function Studies:
(RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid is essential in the study of protein structure and function, as it allows researchers to manipulate and protect specific amino acid residues, such as serine, during experiments. This capability enables a deeper understanding of protein interactions and mechanisms, which can lead to the discovery of new therapeutic targets and strategies.

Upstream product

• 1069-48-3 rac-allylglycine 
• 501-53-1 benzyl chloroformate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 127862-74-2 2-Benzyloxycarbonylamino-pent-4-enoic acid 2,2,2-trifluoro-ethyl ester 
• 149117-84-0 ethyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate 
• 108412-04-0 α-allylglycine hydrochloride 
• 96921-56-1 Allyl N-(benzyloxycarbonyl)glycinate 

Downstream Products

• 106928-49-8 methyl (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoate 
• 475291-55-5 methyl 3-[(benzyloxy)carbonylamino]hex-5-enoate 
• 96921-58-3 methyl 2-[(benzyloxycarbonyl)amino]-4-oxobutanoate 
• 127862-74-2 2-Benzyloxycarbonylamino-pent-4-enoic acid 2,2,2-trifluoro-ethyl ester 
• 406673-07-2 benzyl (1-(methoxy(methyl)amino)-1-oxopent-4-en-2-yl)carbamate 

Relevant academic research and scientific papers

Synthesis and selective N,O-functionalization of pyrazolone-fused 3-aminoazepinones

A new class of pyrazolone-fused 3-amino-1,3,4,7-tetrahydro-2H-azepin-2-ones was synthesized from azepane-based α,β-unsaturated esters. The latter compounds were obtained efficiently from 2-Cbz-amino-N-(2-bromoallyl)-4-pentenamide derivatives through initi

Arginase Inhibitors and Their Therapeutic Applications

Disclosed are small molecule therapeutic compounds that are potent inhibitors of arginase 1 and arginase 2 activity. Also disclosed are pharmaceutical compositions comprising the compounds, and methods for using the compounds for treating or preventing a

Modified N-acyl-homoserine lactones as chemical probes for the elucidation of plant-microbe interactions

Gram-negative bacteria often use N-acyl-homoserine lactones (AHLs) as signal molecules to monitor their local population densities and to regulate gene-expression in a process called "Quorum Sensing" (QS). This cell-to-cell communication allows bacteria to adapt to environmental changes and to behave as multicellular communities. QS plays a key role in both bacterial virulence towards the host and symbiotic interactions with other organisms. Plants also perceive AHLs and respond to them with changes in gene expression or modifications in development. Herein, we report the synthesis of new AHL-derivatives for the investigation and identification of AHL-interacting proteins. We show that our new compounds are still recognised by different bacteria and that a novel biotin-tagged-AHL derivative interacts with a bacterial AHL receptor.

Microbial enantioselective removal of the N-benzyloxycarbonyl amino protecting group

In order to deprotect N-carbobenzoxy-l-aminoacids (Cbz-AA) and related compounds, a series of microorganisms was selected from soil by enrichment cultures with Cbz-l-Glu as sole nitrogen source. A lyophilized whole-cell preparation of two Arthrobacter sp. strains grown on Cbz-Glu or Cbz-Gly exhibited a high cleavage activity. The conditions of hydrolysis have been optimized and a quantitative enantioselective deprotection of several Cbz-dl-amino acids was obtained, as well as the deprotection of N-carbamoylester derivatives of several synthetic amino compounds. The preparation of Cbz-d-allylglycine and l-allylglycine in high yield and high optical purity is described as an application of this method.

Resolution of non-proteinogenic amino acids via microbial lipase-catalyzed enantioselective transesterification

A number of non-proteinogenic amino acids bearing aliphatic side chains were resolved with moderate to good enantioselectivities (E = 15-42) through the Burkholderia cepacia lipase-catalyzed enantioselective transesterification of the 2,2,2-trifluoroethyl esters of their N-benzyloxycarbonyl derivatives with methanol as a nucleophile in diisopropyl ether.

Synthesis of (Optically Active) Sulfur-Containing Trifunctional Amino Acids by Radical Addition to (Optically Active) Unsaturated Amino Acids

Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to α-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H).Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100 percent).The solvent used for the reaction is critical.Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems).The scope of the reaction includes α-substituted α-allylglycine derivative and derivatives as well as β-substituted β-allyl-β-amino alcohols.In the case of optically active α-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H.The products are easily optically enriched by crystallization.Addition of sulfur-based radicals to α-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.

Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids

Porcine pancreatic lipase catalyzed the highly enantioselective hydrolysis of a kind of α-substituted carboxylic esters, i.e., the 2,2,2-trifluoroethyl esters of the N-benzyloxycarbonyl derivatives of unusual amino acids.