L-Aspartic acid α-tert-butyl ester hydrochloride
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L-Aspartic acid α-tert-butyl ester hydrochloride

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A protected L-Aspartic acid. L-Aspartic acid is a non-essential amino acid that has a role as an Escherichia coli metabolite.

Category
L-Amino Acids
Catalog number
BAT-000431
CAS number
176164-02-6
Molecular Formula
C8H15NO4·HCl
Molecular Weight
225.67
IUPAC Name
(3S)-3-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid;hydrochloride
Synonyms
L-Asp-OtBu HCl; (S)-3-Amino-4-(tert-butoxy)-4-oxobutanoic acid hydrochloride
Related CAS
4125-93-3 (free base)
Appearance
White powder
Purity
≥ 99.5% (Chiral purity)
Melting Point
> 200 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C8H15NO4.ClH/c1-8(2,3)13-7(12)5(9)4-6(10)11;/h5H,4,9H2,1-3H3,(H,10,11);1H/t5-;/m0./s1
InChI Key
UIGULSHPWYAWSA-JEDNCBNOSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CC(=O)O)N.Cl

L-Aspartic acid α-tert-butyl ester hydrochloride, a specialized chemical with diverse applications, plays a pivotal role in scientific and industrial settings.

Peptide Synthesis: Serving as a foundational element in peptide and protein construction, L-Aspartic acid α-tert-butyl ester hydrochloride acts as a crucial building block. Its ester group shields the carboxyl function of aspartic acid, preventing undesired side reactions during peptide bond formation. Highly valued for generating intricate peptide sequences, it showcases versatility and significance in both research and therapeutic settings.

Pharmaceutical Intermediate: Positioned as a pivotal intermediate in pharmaceutical drug manufacturing, especially for products involving aspartic acid derivatives, this compound’s ester composition enhances reactivity, facilitating bioactive compound generation. Widely utilized in synthesizing antiviral and anticancer agents among other therapeutic categories, L-Aspartic acid α-tert-butyl ester hydrochloride plays a vital role in pharmaceutical advancement, showcasing its significance in drug development.

Chemical Research: Within chemical research, L-Aspartic acid α-tert-butyl ester hydrochloride is applied in investigating enzyme-substrate interactions and reaction mechanisms. Its distinct structure enables probing aspartic acid behavior across diverse chemical contexts, potentially leading to novel catalyst and reaction path discoveries in chemical synthesis. A key component in expanding understanding of chemical reactions, it highlights its significance in driving chemical advancements.

Chiral Synthesis: In chiral synthesis, this compound serves as a pivotal starting material for generating enantiomerically pure compounds. The ester form provides a convenient means to introduce chiral centers into molecules, a critical element in creating optically active pharmaceuticals. Through utilizing L-Aspartic acid α-tert-butyl ester hydrochloride in stereoselective reactions, chemists can achieve high yields of desired enantiomers, underscoring its importance in chiral synthesis and producing pharmaceutical compounds with distinct optical properties.

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