98045-03-5

Basic information

• Product Name: N-boc Asp(OH)Ome
• Synonyms: N-boc Asp(OH)Ome;N-[(1,1-Dimethylethoxy)carbonyl]-L-aspartic acid alpha-methyl ester;N-tert-Butoxycarbonyl-L-aspartic acid 1-methyl ester;N-Boc-L-aspartic acid 1-Methyl ester, 98%;Boc-L-aspartic acid 1-methyl ester;1-Methyl N-(tert-Butoxycarbonyl)-L-aspartate;(Tert-Butoxy)Carbonyl Asp-OMe;N-tert-Butoxycarbonyla spartic acid a-methylester
• CAS NO: 98045-03-5
• Molecular Formula: C₁₀H₁₇NO₆
• Molecular Weight: 247.24508
• Mol File: 98045-03-5.mol

Chemical Properties

• Melting Point: 79-81℃
• Boiling Point: 407.1±40.0 °C(Predicted)
• Appearance: /Solid
• Density: 1.209
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.09±0.19(Predicted)
• CAS DataBase Reference: N-boc Asp(OH)Ome(CAS DataBase Reference)
• NIST Chemistry Reference: N-boc Asp(OH)Ome(98045-03-5)
• EPA Substance Registry System: N-boc Asp(OH)Ome(98045-03-5)

Safety Data

• Hazardous Substances Data: 98045-03-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-boc Asp(OH)Ome is used as an intermediate in the synthesis of modified alpha-amino acids for the development of novel pharmaceutical compounds. These modified amino acids can exhibit unique biological activities and properties, making them valuable in the design of new drugs with improved efficacy and selectivity.
Used in Peptide Synthesis:
In the field of peptide synthesis, N-boc Asp(OH)Ome is used as a building block for the preparation of peptide-based therapeutics and diagnostic agents. Its Boc protection allows for selective deprotection and coupling reactions, facilitating the assembly of complex peptide sequences with precise control over the reaction conditions.
Used in Organic Synthesis:
N-boc Asp(OH)Ome is also utilized in organic synthesis as a versatile reagent for the preparation of various organic compounds. Its reactivity and functional groups enable a wide range of chemical transformations, making it a valuable tool for the synthesis of target molecules in various research and industrial applications.
Used in the Preparation of 5-cis-alkylprolines:
N-boc Asp(OH)Ome is specifically used as an intermediate in the synthesis of 5-cis-alkylprolines, which are important structural motifs found in various natural products and bioactive compounds. The synthesis of these unique proline derivatives can lead to the development of new pharmaceutical agents with novel modes of action and therapeutic potential.

Upstream product

• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 
• 51186-58-4 4-benzyl Boc-D-aspartate 
• 80963-12-8 α-Methyl β-benzyl (2R)-N-(tert-butoxycarbonyl)aspartate diester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 107020-12-2 methyl N-tert-butyloxycarbonyl-L-azetidine-2-carboxylate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 80963-12-8 4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate 
• 196860-98-7 methyl (S)-2-[(tert-butoxycarbonyl)amino]-3-[3-[(S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl]phenyl]propanoate 
• 67-56-1 methanol 
• 13726-67-5 Boc-Asp-OH 

Downstream Products

• 1379524-36-3 (S,Z)-1-benzyl 6-methyl 2-benzylidene-5-((tert-butoxycarbonyl)amino)-3-oxohexanedioate 
• 1379524-49-8 (S,E)-1-benzyl 6-methyl 5-((tert-butoxycarbonyl)amino)-2-(4-(tert-butyl)benzylidene)-3-oxohexanedioate 
• 1379524-37-4 (S,Z)-1-benzyl 6-methyl 5-((tert-butoxycarbonyl)amino)-2-(4-(tert-butyl)benzylidene)-3-oxohexanedioate 
• 1379524-39-6 (S,Z)-1-benzyl 6-methyl-5-((tert-butoxycarbonyl)amino)-3-oxo-2-(pyren-1-ylmethylene)hexanedioate 
• 1379524-31-8 (S)-6-benzyl 1-methyl 2-((tert-butoxycarbonyl)amino)-4-oxohexanedioate 
• 197720-13-1 (R)-N-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-2-tert-butoxycarbonylamino-succinamic acid methyl ester 
• 1379524-45-4 (R)-6-benzyl 1-methyl 2-((tert-butoxycarbonyl)amino)-4-oxohexanedioate 
• 1207725-92-5 C₁₆H₂₃N₃O₅ 
• 1607459-14-2 C₂₆H₃₇IN₂O₁₂ 
• 162007-06-9 ethyl 3-[[(3S)-(tert-butoxycarbonylamino)-3-(methoxycarbonyl)ethyl]carbamoyl]aminobenzoate 
• 300856-37-5 (S)-tert-Butoxycarbonylamino-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-acetic acid methyl ester 

Relevant articles and documents

Esterase-sensitive prodrugs of a potent bisubstrate inhibitor of nicotinamide n-methyltransferase (Nnmt) display cellular activity

A recently discovered bisubstrate inhibitor of Nicotinamide N-methyltransferase (NNMT) was found to be highly potent in biochemical assays with a single digit nanomolar IC50 value but lacking in cellular activity. We, here, report a prodrug strategy designed to translate the observed potent biochemical inhibitory activity of this inhibitor into strong cellular activity. This prodrug strategy relies on the temporary protection of the amine and carboxylic acid moieties of the highly polar amino acid side chain present in the bisubstrate inhibitor. The modification of the carboxylic acid into a range of esters in the absence or presence of a trimethyl-lock (TML) amine protecting group yielded a range of candidate prodrugs. Based on the stability in an aqueous buffer, and the confirmed esterase-dependent conversion to the parent compound, the isopropyl ester was selected as the preferred acid prodrug. The isopropyl ester and isopropyl ester-TML prodrugs exhibit improved cell permeability, which also translates to significantly enhanced cellular activity as established using assays designed to measure the enzymatic activity of NNMT in live cells.

Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers

Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).

Synthesis of triazole cages containing C3-symmetric α-cyclic tripeptide scaffold

Two water-soluble C3-symmetric 1,2,3-triazole cages containing α-cyclic tripeptide were efficiently synthesized. The key steps include a click reaction to incorporate l-glutamic or l-aspartic acids to a tripodal linker and a unique one-pot cyclotrimerization.

Combined Lewis acid and Br?nsted acid-mediated reactivity of glycosyl trichloroacetimidate donors

Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Br?nsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein.

Structure-guided design of α-amino acid-derived Pin1 inhibitors

The peptidyl prolyl cis/trans isomerase Pin1 is a promising molecular target for anti-cancer therapeutics. Here we report the structure-guided evolution of an indole 2-carboxylic acid fragment hit into a series of α-benzimidazolyl-substituted amino acids.

AMINO ACID INHIBITORS OF CYTOCHROME P450

Methods of inhibiting cytochrome P450 enzymes are provided that can be used for improving the treatment of diseases by preventing degradation of drugs or other molecules by cytochrome P450. Pharmaceutical compositions are provided that can act as boosters

Ruthenium tetroxide oxidation of cyclic N-acylamines by a single layer method: formation of ω-amino acids

The ruthenium tetroxide oxidation of cyclic N-acyl amines by a 10% NaIO4 aqueous solution containing tert-butanol as a single layer system resulted in the endo-cyclic C-N bond cleavage to afford the ω-amino acids as almost sole products in good yields, while a similar oxidation under the double layer using a NaIO4 aqueous solution, and ethyl acetate gave the N-acyl lactams.

Synthesis, characterization and cytolytic activity of α-helical amphiphilic peptide nanostructures containing crown ethers

Many natural α-helical amphiphilic peptides are known to have lytic activity toward different cells. Herein, we describe the synthesis and the characterization of synthetic α-helical amphiphilic peptide nanostructures containing crown ethers, as well as t

Structure-based design of cycloamide-urethane-derived novel inhibitors of human brain memapsin 2 (β-secretase)

A series of novel macrocyclic amide-urethanes was designed and synthesized based upon the X-ray crystal structure. Inhibitors containing 14- to 16-membered rings exhibited low nanomolar inhibitory potencies against memapsin 2. A series of novel macrocycli

Synthesis of non-natural amino acids based on the ruthenium-catalysed oxidation of a phenyl group to carboxylic acid

An efficient method for the synthesis of enantiopure β-, β-, and δ-amino acids with proteinogenic side chains, starting from natural α-amino acids, was developed. The method is based on the ruthenium-catalyzed oxidation of a phenyl group to a carboxylic a