H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH is a protected, amino acid derivative featuring a lysine backbone bearing a gamma-hydroxy substituent on the side chain and an N-terminal amino group, with Boc protection on the lysine side-chain amino functionality to position it for controlled coupling chemistry. The molecule contains both amino and carboxyl functional groups while the gamma-hydroxy group provides an additional hydrogen-bonding and polarity handle, and the DL descriptors indicate a racemic mixture at the stereocenters implied by the name. As a Boc-protected hydroxy-functional lysine analogue, it is used in peptide synthesis workflows and related structure-activity or chemical biology studies where introduction of a hydroxyl-bearing lysine side chain and chemoselective protection of the amine are required.
CAT No: CP26981
CAS No:305820-28-4
Synonyms/Alias:H-DL-delta-Hydroxy-DL-Lys(Boc)-OH;305820-28-4;SCHEMBL12463713;CTK8F0837;H-DL-DELTA-HYDROXY-DL-LYS-OH;AM022058;RT-013201;2-AMINO-6-[(TERT-BUTOXYCARBONYL)AMINO]-5-HYDROXYHEXANOICACID
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH is a protected lysine-derived amino acid ester/acid building block featuring a stereodefined lysine side chain bearing a gamma-hydroxy substituent, along with a Boc-protected -NH2 group on the alpha-amino position. The molecule contains the amino acid backbone with a free carboxylic acid for coupling chemistry, while the Boc group provides orthogonal protection during peptide assembly and can be removed under standard deprotection conditions to expose the amine for subsequent bond formation. The gamma-hydroxyl functionality introduces an additional oxygen nucleophile that can participate in hydrogen bonding, enable selective derivatization, and influence solubility and protecting-group planning. DL stereochemistry at the relevant centers supports use as a chiral or non-chiral intermediate in synthetic campaigns where racemic material is acceptable or where stereochemical resolution and downstream stereochemical control are handled at later stages.
1. Peptide Synthesis
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH is used in peptide synthesis workflows where a lysine side chain is required to carry a gamma-hydroxy handle for post-coupling modification. The Boc-protected alpha-amine supports stepwise peptide coupling without uncontrolled side reactions, while the free carboxylic acid enables formation of amide bonds using standard peptide coupling chemistries. The gamma-hydroxyl group can be retained for aqueous solubility tuning or temporarily protected to prevent competing O-acylation during peptide assembly. Racemic composition can be applied in library generation or in analog series where stereochemical effects are evaluated across later purification or resolution steps, supporting peptide building block preparation and downstream functionalization.
2. Amino Acid Side-Chain Functionalization
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH serves as an amino acid derivatization intermediate for introducing oxygen-containing functionality into lysine-based scaffolds. The gamma-hydroxyl group can undergo selective protection, activation, or conversion to electrophiles suitable for nucleophilic substitution, enabling construction of hydroxy-bearing lysine analogs used in structure-activity relationship studies and chemical biology probes. The Boc group provides a controlled amine protection strategy so that side-chain chemistry can be performed while minimizing interference from the alpha-amino functionality. The resulting functionalized lysine derivatives can be carried forward into conjugation-ready intermediates, peptide analogs, and synthetic organic chemistry sequences that require a stable amino acid core with an orthogonally addressable side chain.
3. Peptidomimetics And SAR Studies
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH is suitable for peptidomimetic construction and SAR studies where lysine-like spacing combined with a gamma-hydroxy group is used to probe binding interactions and conformational preferences. The protected amino acid framework supports incorporation into peptide-like backbones, while the hydroxyl group provides a polar interaction site that can be preserved, masked, or transformed into alternative hydrogen-bonding motifs. Boc protection enables iterative assembly of amide-linked analogs and can be removed to expose the amine for further coupling or for generating branching points in scaffold design. DL stereochemistry can be leveraged for rapid analog generation, with stereochemical outcomes assessed by downstream separation or by comparing matched stereochemical series produced from resolved precursors.
4. Chemical Biology Conjugation
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH can be applied in chemical biology research to generate lysine-based conjugation handles that incorporate an oxygen-functional side chain. The free carboxylic acid supports conversion to activated ester or coupling-ready derivatives, enabling attachment to biomolecule-reactive platforms, while the Boc-protected amine helps maintain chemoselectivity during conjugation preparation. The gamma-hydroxyl group can be exploited for affinity tag design, linker engineering, or orthogonal functional group installation that supports controlled labeling strategies. Downstream derivatives derived from this intermediate can be used to build bioconjugates, affinity reagents, and probe scaffolds where amino acid-derived linkers provide predictable spacing and functional group presentation for molecular recognition experiments.
5. Pharmaceutical Intermediate Preparation
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH is relevant to pharmaceutical intermediate preparation and process chemistry for manufacturing routes that require protected lysine derivatives with a functional side chain. The Boc-protected alpha-amine and free carboxylic acid align with common protected amino acid strategies used to control chemoselectivity during scale synthesis of peptide fragments, peptidomimetic intermediates, and side-chain-modified building blocks. The gamma-hydroxyl functionality enables downstream conversion into protected or activated forms that can be carried into later steps for coupling, cyclization, or linker installation in drug-substructure assembly. Racemic input may be acceptable for intermediate stages where stereochemical specification is addressed by later resolution, stereospecific transformations, or by selecting stereochemically defined downstream coupling partners.
6. Analytical Research Standards
H-DL-gamma-Hydroxy-DL-Lys(Boc)-OH can function as an analytical research standard and method-development reference for amino acid derivatization, peptide fragment characterization, and side-chain functional group monitoring. The presence of a Boc-protected amine and a free carboxylic acid provides distinct chemical signatures that can be tracked by chromatographic and spectrometric workflows during protected amino acid synthesis and deprotection studies. The gamma-hydroxyl group contributes characteristic polarity and derivatization behavior, supporting method optimization for detecting hydroxy-functional lysine motifs in complex mixtures. Downstream conversion to defined derivatives can support calibration, impurity profiling, and verification of peptide coupling outcomes in synthetic methodology development and industrial quality control contexts.
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