3-Amino-L-tyrosine dihydrochloride monohydrate

3-Amino-L-tyrosine dihydrochloride monohydrate is a protected-free amino acid salt form of L-tyrosine, featuring the canonical α-amino and α-carboxyl groups alongside a phenolic side chain on the aromatic ring. The molecule contains two chloride counterions associated with the amino acid functional groups and includes one molecule of water of hydration, with the stereochemistry indicated as L at the α-carbon. This dihydrochloride monohydrate is used as a defined, water-compatible tyrosine source for peptide synthesis workflows and for preparing tyrosine-containing amino acid derivatives in solution-phase or solid-phase assembly, as well as for analytical method development where controlled salt form and hydration state can affect handling and solubility.

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

CAT No: CP17501

CAS No:23279-22-3

Synonyms/Alias:23279-22-3;3-Amino-L-tyrosine dihydrochloride;(S)-2-Amino-3-(3-amino-4-hydroxyphenyl)propanoic acid dihydrochloride;SCHEMBL304140;CTK7I3490;MolPort-006-701-261;SBB063957;AKOS015889893;RTR-010849;AK117404;DB-046118;TR-010849;ST24035960;H-Tyr(3-NH2)-OH.2HCl;3-Amino-L-tyrosine dihydrochloride monohydrate;L-Tyrosine, 3-amino-, dihydrochloride (9CI);3-Amino-L-tyrosine DiHCl;(S)-2-Amino-3-(3-amino-4-hydroxyphenyl)propanoic acid dihydrochloride;H-3-Amino-Tyr-OH 2 HCl;MFCD00012964;3-Amino-Tyr-OH.2HCl;C9H14Cl2N2O3;(2S)-2-amino-3-(3-amino-4-hydroxyphenyl)propanoic acid dihydrochloride;AKOS015889893;CS-W012402;HY-W011686;AS-65785;PD167631;L-TYROSINE, 3-AMINO-, 2HCL (9CI);A12311;M03158

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M.F/Formula
C9H14Cl2N2O3
M.W/Mr.
287.14
Sequence
Three Letter Code:H-Tyr(3-NH2)-OH.2HCl

3-Amino-L-tyrosine dihydrochloride monohydrate is a tyrosine-derived amino acid building block featuring an additional amino substituent on the aromatic ring, supplied as a dihydrochloride salt with one hydrate. This salt form increases handling robustness for solid reagents and supports reproducible performance in peptide and medicinal chemistry workflows where the free amino functionality is required for downstream coupling or functionalization. The L-configuration and phenolic side chain make it a useful scaffold for constructing aromatic, amino-substituted motifs in peptides, peptidomimetics, and heteroaromatic/amine-rich intermediates.

1. Peptidomimetic Building Blocks

3-Amino-L-tyrosine dihydrochloride monohydrate is used by peptide chemists and medicinal chemistry groups to introduce an aromatic ring bearing both a phenolic hydroxyl and an additional aniline-like amino group into custom peptides and peptidomimetics. The extra amino functionality enables incorporation into amide-forming sequences after appropriate derivatization, supporting the synthesis of side-chain functionalized analogs used for structure-activity relationship studies and receptor/ligand binding investigations in chemical biology programs. The dihydrochloride salt form is particularly valued when consistent, weighable reagent behavior is needed for multi-step assembly and when the compound is carried through coupling and purification workflows as a stable intermediate.

2. Pharmaceutical Intermediate Development

3-Amino-L-tyrosine dihydrochloride monohydrate serves as a practical starting material for preparing amine-rich aromatic intermediates used in medicinal chemistry and specialty chemical manufacturing. The combination of the phenolic group and ring amino functionality supports conversion into diversified heteroaryl and amino-substituted scaffolds that are common in kinase inhibitor, GPCR ligand, and other small-molecule discovery chemistries where an aniline-like handle is required for further derivatization. Researchers often select this specific tyrosine-derived scaffold to access aromatic substitution patterns that are difficult to reproduce from simpler tyrosine derivatives, enabling targeted late-stage functional group installation during lead optimization.

3. Analytical Standard Synthesis

3-Amino-L-tyrosine dihydrochloride monohydrate is frequently used to prepare analytical standards for method development and quality control in laboratories performing amino acid profiling, LC-MS quantitation, and related analytical workflows. The defined L-stereochemistry and the presence of both phenolic and additional amino functionality make it a relevant reference for verifying retention behavior and ionization response of amino acid derivatives that contain aromatic amine substitution. Because it is supplied as a dihydrochloride monohydrate, it is commonly selected when reproducible preparation of stock solutions and consistent salt-state behavior are important for calibration and system suitability checks.

4. Chemical Biology Probe Precursors

3-Amino-L-tyrosine dihydrochloride monohydrate is used as a precursor for chemical biology reagent development where aromatic amino substitution provides a handle for conjugation or further derivatization. Teams working on affinity tags, linker modules, and small-molecule probes leverage the phenolic hydroxyl and ring amino group to build functionalized intermediates that can be coupled to carriers, surfaces, or detection moieties after appropriate protection/activation steps. This reagent is particularly relevant when the design requires an aromatic scaffold derived from tyrosine chemistry, enabling incorporation of amino-substituted aromatic motifs into probe architectures used for target engagement and interaction mapping workflows.

Abbr
H-Tyr(3-NH2)-OH.2HCl.H2O
InChI
1S/C9H12N2O3.2ClH/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14;;/h1-3,7,12H,4,10-11H2,(H,13,14);2*1H/t7-;;/m0../s1
InChI Key
PIFWBMTWCTUOOQ-KLXURFKVSA-N
Canonical SMILES
C1=CC(=C(C=C1CC(C(=O)O)N)N)O.Cl.Cl

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