Boc-L-Lys-OMe*AcOH

Boc-L-Lys-OMe*AcOH is a protected amino acid derivative based on L-lysine in which the α-amino group is masked with a Boc (tert-butoxycarbonyl) protecting group and the carboxyl functionality is present as a methyl ester (Lys-OMe). The lysine side chain retains its ε-amino functionality, while the molecule is supplied as an acetate-associated form (*AcOH), which reflects a counterion/association state rather than a change to the core amino acid connectivity. Boc-L-Lys-OMe*AcOH is used as a stepwise building block in peptide synthesis and related amide bond-forming sequences, where the Boc group supports chemoselective handling of the α-amino group and the ester form provides controlled reactivity for downstream transformations.

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

CAT No: CP25898

CAS No:55757-60-3

Synonyms/Alias:55750-62-4;N-Succinimidyl3-maleimidopropionate;2,5-Dioxopyrrolidin-1-yl3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate;3-(Maleimido)propionicacidN-hydroxysuccinimideester;BMPS;N-(3-Maleimidopropionyloxy)succinimide;(2,5-dioxopyrrolidin-1-yl)3-(2,5-dioxopyrrol-1-yl)propanoate;3-MaleimidopropionicAcidN-SuccinimidylEster;3-MaleimidopropionicacidN-hydroxysuccinimideester;2,5-dioxopyrrolidin-1-yl3-(2,5-dioxopyrrol-1-yl)propanoate;N-Maleoyl-beta-alanineN-hydroxysuccinimideester;N-Maleoyl-beta-alanineN'-hydroxysuccinimideester;3-maleimidopropionicacidn-hydroxysuccinimide-ester;AC1NEOFI;PubChem19903;SCHEMBL157545;3-MaleimidopropionicacidNHS;358657_ALDRICH;succinimido3-maleimidopropanoate;3-Maleimido-propionicNHSester;63179_FLUKA;358657_SIGMA;JKHVDAUOODACDU-UHFFFAOYSA-N;MolPort-003-848-459;C11H10N2O6

Chemical Name:N-alpha-t-Butyloxycarbonyl-L-lysine methylester acetate

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M.F/Formula
C11H10N2O6
M.W/Mr.
260,33*60,05 g/mole

Boc-L-Lys-OMe*AcOH is a protected lysine derivative featuring an N-terminal Boc (tert-butoxycarbonyl) group and a methyl ester at the C-terminus, supplied as an acetic acid salt form. This combination makes it a practical amino acid building block for controlled incorporation of Lys side-chain chemistry during peptide assembly, while the ester and Boc protection help maintain functional-group stability through coupling and purification steps. The protected lysine side chain is well aligned with routine peptide synthesis workflows where the terminal groups must remain masked until the desired stage of deprotection.

1. Solid-Phase Peptide Synthesis

Boc-L-Lys-OMe*AcOH is frequently selected for segment construction in solid-phase peptide synthesis workflows that require a lysine residue with a protected amino terminus and a C-terminal ester handle for downstream transformations. Peptide chemists use this building block when assembling peptides and peptide fragments where lysine's basic side chain must be carried through coupling steps without uncontrolled reactivity. The Boc protection supports standard peptide assembly conditions, while the ester form is useful for preparing peptide intermediates that are later converted into acids or further functionalized depending on the target sequence design.

2. Lysine-Containing Peptide Fragments

Boc-L-Lys-OMe*AcOH supports preparation of lysine-containing peptide fragments used in custom peptide manufacturing and research-grade peptide libraries. In these workflows, the derivative's protected termini allow chemists to manage reactivity during fragment condensation and purification, enabling reliable assembly of sequences that include a lysine residue at defined positions. Researchers commonly rely on this type of lysine building block when they need a consistent, protected lysine unit to build longer constructs, including peptide segments used for subsequent deprotection and final peptide finishing.

3. Pharmaceutical Intermediate Development

Boc-L-Lys-OMe*AcOH is also used as a pharmaceutical intermediate building block in medicinal chemistry programs that require protected lysine motifs for peptidomimetic or peptide-like structures. Chemical development teams often choose Boc-protected amino acid derivatives to control functional-group compatibility across multi-step synthesis, particularly when the lysine residue must be introduced late in the route or incorporated into a larger intermediate framework. The acetic acid salt form can be advantageous for handling and formulation during intermediate preparation, supporting reproducible downstream conversion to acids or other activated forms used in further synthetic elaboration.

4. Peptide Library and SAR Studies

Boc-L-Lys-OMe*AcOH is employed in peptide library synthesis where lysine-containing variants are generated to support structure-activity relationship studies in chemical biology and medicinal chemistry research. By using a protected lysine building block with defined terminal protection, researchers can systematically vary surrounding residues while maintaining consistent lysine incorporation chemistry. This approach is particularly useful when building a set of related peptide analogs or peptide fragments that require reliable coupling performance and controlled deprotection timing to access the desired final functional groups for assay-ready materials.

Size
5 g;25 g;
InChI
1S/C11H10N2O6/c14-7-1-2-8(15)12(7)6-5-11(18)19-13-9(16)3-4-10(13)17/h1-2H,3-6H2
InChI Key
JKHVDAUOODACDU-UHFFFAOYSA-N
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)CCN2C(=O)C=CC2=O

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