1231709-25-3

Basic information

• Product Name: (R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98% ee, 98%
• Synonyms: (R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98% ee, 98%;(R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98%, 98% ee;α-Me-D-Asp(OtBu)-OH;H-alpha-Me-D-Asp(tBu)-OH;(R)-α-Methylaspartic acid-4-tert-butyl ester, 98% ee;(2R)-2-amino-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid;Alpha-Methyl-D-Asp(OtBu)-OH
• CAS NO: 1231709-25-3
• Molecular Formula: C9H17NO4
• Molecular Weight: 203
• Product Categories: α-Methyl Amino Acids
• Mol File: 1231709-25-3.mol
• Article Data: 2

Chemical Properties

• Appearance: White to pale yellow/Powder
• CAS DataBase Reference: (R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98% ee, 98%(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98% ee, 98%(1231709-25-3)
• EPA Substance Registry System: (R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98% ee, 98%(1231709-25-3)

Safety Data

• Statements: 45-46-11-65
• Safety Statements: 53-23-24-45
• TSCA: No
• Hazardous Substances Data: 1231709-25-3(Hazardous Substances Data)

Usage

General Description

"(R)-alpha-Methylaspartic acid-4-tert-butyl ester, 98% ee, 98%" is a chemical compound with a purity of 98%. It is a derivative of aspartic acid, a nonessential amino acid that is important for the synthesis of proteins and the functioning of the central nervous system. The presence of the (R) enantiomer indicates that it is a chiral compound, meaning it has a specific three-dimensional structure. The tert-butyl ester group attached to the molecule provides stability and increased lipophilicity, which makes it useful for various synthetic and biological applications. The high enantiomeric excess (ee) of 98% indicates a high level of purity and the compound's potential for use in asymmetric synthesis and other chemical processes.

Upstream product

• 135923-94-3 O⁴-(tert-Butyl) Hydrogen (S)-N²-<(Benzyloxy)carbonyl>-2-methylaspartate 
• 135923-97-6 O⁴-(tert-Butyl) Hydrogen (R)-N²-<(Benzyloxy)carbonyl>-2-methylaspartate 

Downstream Products

• 1072845-47-6 (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-succinic acid 4-tert-butyl ester 

Relevant articles and documents

Synthesis and utilization of chiral α-methylated α-amino acids with a carboxyalkyl side chain in the design of novel Grb2-SH2 peptide inhibitors free of phosphotyrosine

The growth factor receptor-bound protein 2 (Grb2) is an SH2 domain-containing docking module that represents an attractive target for anticancer therapeutic intervention. To improve the potency and bioavailability of the Grb2-SH2 inhibitors, the chiral α-methyl-α-carboxyalkyl amino acid [(α-Me)Aa] was designed to cover dual structural and functional features separately contributed by 1-aminocyclohexanecarboxylic acid (Ac6c) and α-aminoadipic acid (Adi) in position Y + 1. The enantiopure L(or D)-(α-Me)Aa bearing various chain length carboxylalkyl side chain was conveniently synthesized by an optimized oxazolidinone methodology. The incorporation of (S)-(α-Me)Aa into the non-pTyr-containing peptide framework with a 5-amino acid sequence binding motif of X-2-Leu- (3′-substituted-Tyr)0-X+1-Asn really improved the inhibitory activity, affording potent (R)-sulfoxide-bridged cyclic and an open-chain series of pentapeptide inhibitors of Grb2-SH2 domain (IC50 = 1.1-5.8 μM). More significantly, these (α-Me)Aa incorporated peptide inhibitors showed excellent activities in inhibiting the growth of erbB2-dependent MDA-MB-453 tumor cell lines with low micromolar IC50 values, owing to the reduced peptidic nature and absence of pTyr or pTyr mimetics.