H-Abu-OMe · HCl

H-Abu-OMe · HCl is a hydrochloride salt of an amino acid methyl ester derived from 2-aminobutyric acid (Abu), featuring an amino group and a carboxyl functionality converted to a methyl ester (-COOCH3) along with a branched alkyl side chain. The molecule bears the esterified carboxyl group and an amino group present as a hydrochloride salt (-NH3+ Cl−), which alters its protonation state relative to the free amino acid and can influence solubility and handling during synthesis. H-Abu-OMe · HCl is used as a protected-free amino acid ester building block in solution-phase or solid-phase peptide synthesis workflows and as a substrate for preparing further amino acid derivatives, including side-chain and backbone functionalization studies.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP26422

CAS No:15399-22-1

Synonyms/Alias:(S)-methyl2-aminobutanoate;15399-22-1;Methyl(2S)-2-Aminobutanoate;SCHEMBL172701;MolPort-023-220-043;ZZWPOYPWQTUZDY-BYPYZUCNSA-N;ZINC35186321;AKOS017404988;(S)-2-Aminobutanoicacidmethylester;AJ-90757;AK158355;CJ-18640;DB-013745;FT-0661633;M-3739

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M.F/Formula
C5H11NO2
M.W/Mr.
153.61

H-Abu-OMe · HCl is the hydrochloride salt of an L-α-aminobutyric acid methyl ester (H-Abu-OMe), where the amino group is protonated as a chloride salt and the carboxyl functionality is masked as a methyl ester. The molecule is a chiral amino acid derivative with a stereogenic center at the α-carbon, and its side chain is a short aliphatic chain that supports straightforward incorporation into peptide-like structures or conversion into other amino acid building blocks. The ester and salt-protected amine combination provides a controlled reactivity profile for peptide coupling planning, while the hydrochloride form can facilitate handling and salt-stabilized storage of the amine. The compound functions as a chiral intermediate for amino acid derivatization, including routes to protected amino acids, alternative ester forms, and side-chain modified analogs used in synthetic organic chemistry and biochemical research.

1. Protected Amino Acid Synthesis

H-Abu-OMe · HCl supports protected amino acid synthesis workflows by providing an α-amino ester precursor whose amine can be converted into N-protected derivatives compatible with peptide coupling chemistry. The methyl ester enables ester-exchange or deprotection strategies to reach the corresponding carboxylic acid stage when needed for activation and coupling, while the α-amino functionality can be selectively protected using standard orthogonal protection logic. The stereogenic center in the amino acid backbone allows retention of configuration through intermediate transformations, which is important for stereochemically defined peptide building block preparation. Downstream conversion to N-protected Abu derivatives can be applied to fine chemical synthesis and process chemistry intermediate preparation where controlled functional-group timing is required.

2. Peptide Coupling Chemistry

H-Abu-OMe · HCl is applicable to peptide synthesis planning as an amino acid ester precursor that can be transformed into activated amino acid derivatives or into protected amino acids for stepwise chain assembly. The α-amino group and ester functionality enable coupling strategy design, including temporary protection of the amine and conversion of the ester to a carboxylate for amide bond formation. The aliphatic side chain and chiral α-center make the derivative suitable for constructing peptide motifs that incorporate Abu residues or for generating peptide analogs with altered backbone sterics. Peptide building block preparation from this intermediate can be used in combinatorial library synthesis and structure-activity relationship studies where defined stereochemistry and functional-group compatibility are required for reproducible coupling.

3. Unnatural Amino Acid Incorporation

H-Abu-OMe · HCl can serve in chemical biology and peptidomimetic construction as a chiral amino acid intermediate for generating unnatural amino acid analogs bearing Abu-derived backbones. The methyl ester and salt form provide a handle for controlled functional group interconversions, such as ester hydrolysis to the acid, N-protection for orthogonal peptide chemistry, and subsequent side-chain derivatization to tune hydrophobicity or conformational preferences. The short aliphatic side chain supports incorporation into peptide-like scaffolds where backbone rigidity or steric effects are modulated without introducing additional aromatic or strongly polar groups. The resulting derivatives can be used to generate stereochemically defined analogs for molecular design and SAR studies, supporting downstream synthesis of constrained or modified peptide structures.

4. Chiral Intermediate Manufacturing

H-Abu-OMe · HCl is suitable for industrial and process chemistry contexts as a chiral amino acid intermediate that can be routed into multiple derivative classes through functional-group programming. The hydrochloride salt form provides a practical starting point for downstream transformations that require a controlled amine state, while the methyl ester supports conversion to alternative ester forms or to carboxylic acid intermediates used in manufacturing routes. The defined stereochemistry at the α-carbon enables consistent feedstock behavior for producing protected amino acids, peptide coupling reagents, and other chiral building blocks used in specialty chemical production. The compound's structural simplicity and functional-group accessibility make it compatible with scalable intermediate preparation where reproducible conversion to protected derivatives is required.

5. Analytical Standards Development

H-Abu-OMe · HCl can be employed in analytical research for method development and reference material preparation related to amino acid ester and amino acid salt chemistry. The presence of both an α-amino ester motif and a defined stereocenter allows it to function as a structural comparator for monitoring derivatization steps, salt formation, and ester-to-acid conversion in synthetic workflows. The hydrochloride form can also support calibration or verification of chromatographic behavior for amino acid derivatives under conditions where protonation state matters. Analytical application of this intermediate aligns with amino acid derivatization studies and quality control of peptide building block preparation, supporting reliable identification of stereochemically defined intermediates in fine chemical synthesis.

Size
5 g;25 g;
InChI
1S/C5H11NO2/c1-3-4(6)5(7)8-2/h4H,3,6H2,1-2H3/t4-/m0/s1
InChI Key
ZZWPOYPWQTUZDY-BYPYZUCNSA-N
Canonical SMILES
CCC(C(=O)OC)N

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