L-Arginine methyl ester dihydrochlorid is the methyl ester hydrochloride salt of L-arginine, featuring the α-amino acid backbone with an arginine guanidinium-containing side chain and a carboxyl group converted to a methyl ester. The molecule bears an α-amino group and a guanidinium functional group, with both basic sites present as hydrochloride salts (dihydrochloride) and the carboxyl functionality masked by esterification to alter polarity and reactivity relative to the free amino acid. As an amino acid ester, it is commonly employed as a protected-like, stepwise building block for peptide synthesis and for preparing arginine-containing derivatives in solution or solid-phase workflows where controlled carboxyl activation and side-chain functionality are required.
CAT No: CP00241
CAS No:26340-89-6
Synonyms/Alias:26340-89-6;L-Argininemethylesterdihydrochloride;H-Arg-OMe.2HCl;MethylL-argininatedihydrochloride;H-Arg-OMe2HCl;(S)-Methyl2-amino-5-guanidinopentanoatedihydrochloride;SBB066039;methyl(2S)-2-amino-5-carbamimidamidopentanoatedihydrochloride;11030_FLUKA;L-Arginine,methylester,dihydrochloride;PubChem18611;L-Arginine,methylester,hydrochloride(1:2);AC1L3LKE;AC1Q3B1D;C7H18Cl2N4O2;KSC786I5P;11030_ALDRICH;SCHEMBL940540;CTK6I6457;2577-94-8(Parent);MolPort-003-925-882;XQYZOBNLCUAXLF-XRIGFGBMSA-N;ACT07708;EINECS247-622-0;ANW-25974
L-Arginine methyl ester dihydrochlorid is the methyl ester hydrochloride salt of L-arginine, featuring the canonical L-configuration at the α-carbon and a guanidinium-containing side chain that is protonated under typical synthetic conditions. The molecule combines an esterified carboxyl group with a strongly basic, resonance-stabilized guanidine functionality, yielding a cationic, water-compatible profile that can be handled as a crystalline salt. The two hydrochloride counterions support salt formation and can influence solubility, coupling behavior, and acid-base equilibria during peptide synthesis and derivatization. As an amino acid ester, the compound functions as a chiral, protected-by-ester carboxyl precursor that can be converted into amide-forming intermediates and downstream arginine-containing building blocks while preserving stereochemical integrity.
1. Peptide Synthesis
L-Arginine methyl ester dihydrochlorid is used in peptide building-block workflows where arginine residues must be introduced into growing chains with controlled side-chain basicity. The methyl ester masks the C-terminus as an ester, enabling selective conversion to activated carboxyl derivatives for amide bond formation while the guanidinium group remains compatible with standard coupling strategies that account for its strong basicity. Salt-state guanidinium can be managed through base selection and orthogonal protection logic when preparing protected arginine analogs for N-to-C coupling. The resulting arginine-containing peptide intermediates support synthesis of protected peptide fragments, linear peptide libraries, and arginine-rich sequences for biochemical research and process-scale peptide manufacturing development.
2. Side-Chain Functionalization
L-Arginine methyl ester dihydrochlorid is applicable to side-chain modification chemistry targeting the guanidinium functionality for generating functionalized arginine derivatives. The stereochemically defined α-amino ester provides a stable platform for transformations that may include guanidine derivatization, conversion to alternative cationic motifs, or incorporation into scaffolds requiring persistent positive charge. Ester-to-amide or ester-to-acid interconversions can be paired with guanidine-reactive steps to produce arginine analogs suitable for receptor-binding studies, enzyme-substrate analogs, or charge-tuned biomolecule probes. Downstream derivatives can be carried forward into peptidomimetics and chemical biology reagents where controlled basicity and defined stereochemistry are required.
3. Chemical Biology Probes
L-Arginine methyl ester dihydrochlorid serves as a chiral amino acid intermediate for constructing chemical biology tools that rely on arginine-like cationic recognition. The guanidinium group supports electrostatic interactions and can be used to design labeling handles or affinity motifs, while the methyl ester enables conversion into amide-linked probes or incorporation into peptide conjugates. Salt form handling can facilitate coupling to activated electrophiles under conditions that preserve the L-configuration and minimize racemization at the α-center. The resulting arginine-containing probe scaffolds can be used for biomolecular interaction mapping, cellular uptake studies of labeled peptides, and analytical reagent preparation where defined stereochemistry and charge distribution matter.
4. Protected Amino Acid Preparation
L-Arginine methyl ester dihydrochlorid is suitable for downstream conversion into protected arginine building blocks used in orthogonally protected peptide synthesis. The amino ester form allows controlled functional group interconversion, including hydrolysis to the corresponding acid or activation to carboxyl derivatives that can be coupled after installing appropriate guanidine protection schemes. The presence of the guanidinium group as a salt can be leveraged during protection/deprotection planning to maintain compatibility with Fmoc- or Boc-based peptide assembly strategies. Manufactured protected arginine intermediates derived from this ester can feed fine chemical synthesis of peptide segments, combinatorial libraries, and industrial peptide intermediates requiring consistent stereochemical quality.
5. Process Chemistry Intermediate
L-Arginine methyl ester dihydrochlorid is employed as a chiral, salt-form amino acid ester intermediate in process chemistry routes that require reliable handling and reproducible downstream conversion to arginine-containing products. The ester functionality provides a convenient handle for staged transformations, enabling process designs that separate guanidine chemistry from C-terminal activation steps to manage reactivity and control impurity profiles. The defined L-stereocenter supports stereochemically consistent manufacturing of peptide building blocks and arginine-derived specialties. Downstream use can include preparation of activated carboxyl intermediates, conversion to acid forms for coupling, and feeding into larger-scale peptide synthesis or specialty chemical production where amino acid derivative consistency is essential.
6. Analytical Standards
L-Arginine methyl ester dihydrochlorid can be used to prepare analytical reference materials for amino acid and peptide method development, including chromatographic and mass spectrometric workflows. The combination of an amino ester and guanidinium functionality produces characteristic ionization behavior that supports identification and quantification of arginine-containing species and related derivatives. Salt-state form can improve reproducibility in sample preparation and calibration when monitoring ester-to-amide conversion, hydrolysis, or coupling-related transformations. The compound-derived standards and internal calibrants support quality control of peptide intermediates, verification of derivatization completeness, and method validation for amino acid derivative analysis in research and industrial laboratories.
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