Ac-D-Lys-OH is an N-acetylated derivative of D-lysine (a basic, proteinogenic amino acid) containing a side-chain ε-amino group characteristic of lysine and a free carboxylic acid group. The molecule bears an acetyl protecting group on the α-amino functionality, yielding an amide that reduces α-amino reactivity while retaining the ε-amino group for further derivatization or selective functionalization, and its stereochemistry is specified as D at the α-carbon. As a protected amino acid building block, Ac-D-Lys-OH is used in peptide and amino acid derivative synthesis and in chemical biology workflows where incorporation of D-lysine with controlled α-amino protection and a remaining side-chain amine handle is required.
CAT No: CP27244
CAS No:58840-79-2
Synonyms/Alias:58816-66-3;3-(4-nitrophenyl)-L-alanineethylesterhydrochloride;3-(4-nitro-phenyl)-l-alanineethylesterhcl;Ethyl4-nitro-3-phenyl-L-alaninatemonohydrochloride;(S)-ethyl2-amino-3-(4-nitrophenyl)propanoatehydrochloride;3-(4-nitro-phenyl)-L-alanineethylesterhydrochloride;ethyl(2S)-2-amino-3-(4-nitrophenyl)propanoatehydrochloride;(S)-ETHYL2-AMINO-3-(4-NITROPHENYL)PROPANOATE(HYDROCHLORIDE);h-4-nitro-phe-oethcl;h-phe(4-no2)-oethcl;AC1O57Y8;SCHEMBL1859938;CTK1H4042;HHZUMTWHYNIFOC-PPHPATTJSA-N;MolPort-006-709-492;CS-M0206;EINECS261-455-0;ANW-48413;AKOS015920489;AS06694;Ethyl4-nitro-3-phenyl-L-alaninateHCl;H-PHE(4-NO2)-OETHYDROCHLORIDE;AK-45901;BR-45901;KB-63585
Ac-D-Lys-OH is an N-acetylated D-lysine amino acid with a free carboxylic acid and a side-chain primary amine on the lysine residue. This stereochemically defined, protected N-terminus makes it a practical building block for peptide and peptidomimetic work where D-configuration at the alpha carbon is required to probe stereochemical effects, proteolysis resistance, or conformational outcomes. In many workflows, the N-acetyl group provides a controlled "blocked" amine at the peptide N-terminus while leaving the lysine side chain available for further derivatization or coupling.
1. Peptidomimetic Building Block
Ac-D-Lys-OH is used by peptide chemists and medicinal chemistry teams to assemble D-amino acid-containing peptide analogs and peptidomimetics where lysine's side-chain functionality must remain accessible for downstream modification. The N-acetylated alpha-amine helps standardize the N-terminal chemistry across libraries, while the D-configuration supports structure-activity relationship studies that compare stereochemical variants. Researchers commonly incorporate this residue into solution-phase or solid-phase peptide sequences and then use the lysine side-chain amine for selective functionalization, such as installing solubilizing groups, affinity handles, or further protected derivatives for multi-step assembly.
2. Lysine Side-Chain Functionalization
Ac-D-Lys-OH is frequently selected as a lysine-derived intermediate for preparing amine-reactive derivatives and conjugation-ready building blocks. With the side-chain primary amine present, it can be used to generate N- or side-chain substituted lysine analogs for subsequent coupling to activated esters, isothiocyanates, aldehydes, or other electrophiles used in chemical biology workflows. The N-acetyl protection pattern helps prevent unintended N-terminus reactivity during derivatization steps, enabling more controlled downstream modification of the lysine side chain in materials research, affinity reagent development, and peptide-linker construction.
3. Analytical Reference and Standards
Ac-D-Lys-OH is useful for analytical method development and characterization workflows that require a defined D-lysine-containing reference material. Laboratories using LC-MS, amino acid profiling, or peptide hydrolysis/derivatization strategies often rely on stereochemically specified amino acid controls to evaluate recovery, derivatization efficiency, and chromatographic behavior for D-configured lysine residues. The N-acetylated form provides a distinct chemical signature relative to free lysine, supporting method validation when distinguishing N-acetylated lysine species or monitoring D-amino acid-containing samples.
4. Stereochemical Control In Synthesis
Ac-D-Lys-OH supports synthetic programs that need explicit stereochemical control at the lysine alpha center, especially in D-amino acid-enriched peptide analogs used for mechanistic studies and sequence optimization. Chemical development groups use this residue to systematically vary stereochemistry while keeping the lysine side-chain chemistry consistent across analogs, which is valuable when comparing how D-configuration influences stability and sequence-dependent properties. The combination of an N-acetylated backbone amine and a free side-chain amine makes it a convenient starting point for building stereodefined intermediates that feed into larger peptide or conjugate synthesis campaigns.
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