Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH is a protected, non-natural alanine derivative featuring an Fmoc carbamate on the α-amino functionality and a Boc-protected side-chain amino group within a β-(1-piperazinyl) substituted framework. The molecule contains a free carboxylic acid for coupling chemistry, while the piperazine ring provides a basic, nitrogen-rich side-chain handle and the Boc group masks one piperazine nitrogen to control chemoselectivity during peptide assembly. Employed as a building block for stepwise peptide synthesis and related structure-activity studies, it enables incorporation of a piperazine-bearing alanine analogue into peptide chains while maintaining orthogonal protection patterns for selective deprotection and subsequent functionalization.
CAT No: CP26986
CAS No:313052-20-9
Synonyms/Alias:313052-20-9;(S)-4-[2-CARBOXY-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-ETHYL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;(S)-3-(4-Boc-piperazin-1-yl)-2-(fmoc-amino)propionic acid;Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(tert-butoxycarbonyl)piperazin-1-yl)propanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]propanoic acid;MFCD01860747;(S)-3-(4-Boc-piperazin-1-yl)-2-(Fmoc-amino)-propionic acid;Fmoc--(1-piperazinyl)-Ala(Boc)-OH;FB49940;Fmoc-b-(1-piperazinyl)-L-Ala(Boc)-OH;BS-50888;CS-0210634;E70599;S-313052-20-9;(2S)-3-[4-(TERT-BUTOXYCARBONYL)PIPERAZIN-1-YL]-2-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}PROPANOIC ACID;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(tert-butoxycarbonyl)piperazin-1-yl)propanoicacid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(tert-butoxycarbonyl)piperazin-1-yl)propanoic acid;
Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH is a protected, chiral amino acid derivative designed for peptide chemistry, featuring an alanine stereocenter bearing an N-Fmoc group and a side-chain piperazine substituent at the beta position, alongside a Boc-protected amino functionality on the alanine side. The molecule contains a carbamate-protected amine (Boc) and a fluorenylmethoxycarbonyl protecting group (Fmoc) that together regulate amide bond formation and control orthogonal deprotection sequences. The piperazine ring introduces a basic, nucleophilic heterocycle with two tertiary amine nitrogens that can participate in salt formation, nucleophilic substitution, and subsequent functional group elaboration. The presence of both protected carboxyl and amino elements makes the compound a stable chiral intermediate for protected amino acid synthesis and downstream incorporation into peptide-based scaffolds.
1. Peptide Synthesis
Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH supports solid-phase peptide synthesis and related coupling workflows by providing an Fmoc-protected amino terminus for controlled chain elongation while the Boc group on the additional amine functionality helps prevent undesired side reactions during coupling. The beta-(1-piperazinyl) substituent introduces a heterocycle that can be carried through peptide assembly without losing stereochemical integrity at the alanine center. Orthogonal deprotection strategies enable stepwise removal of Fmoc under base to reveal the reactive amine for peptide bond formation, while Boc can be managed to expose the piperazine-associated amine only when required for conjugation or further derivatization. The resulting peptide building block construction enables preparation of amino acid sequences and peptidomimetic fragments bearing a defined, protonatable side chain for subsequent structure-function studies.
2. Bioconjugation Chemistry
Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH is suitable for bioconjugation workflows where a basic piperazine handle is used to tune solubility, charge state, and reactivity toward electrophilic coupling partners. The protected amino groups (Fmoc and Boc) allow the compound to be incorporated into peptide carriers or linker intermediates with controlled exposure of nucleophilic nitrogens at defined stages. Deprotection of the Boc group can reveal an additional amine for nucleophilic substitution or amide/urea formation, while the piperazine nitrogens can enable salt formation and can be further functionalized to introduce leaving groups or reactive moieties. The chiral alanine backbone and protected-group strategy support generation of well-defined conjugation intermediates for chemical biology and biomolecule modification.
3. Peptidomimetics And SAR
Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH can be employed in peptidomimetic construction and structure-activity relationship studies by embedding a stereochemically defined alanine unit bearing a beta-attached piperazine that mimics common cationic pharmacophore motifs. The Fmoc/Boc protection pattern supports iterative synthesis of analog libraries where side-chain amine exposure is timed to match the desired diversification step. The piperazine ring enables downstream derivatization such as N-alkylation, acylation, or conversion to substituted heterocycles, allowing systematic variation of basicity and steric environment while maintaining the same backbone stereochemistry. The resulting analogs can serve as chemically consistent building blocks for SAR-driven scaffold refinement and medicinal chemistry intermediate preparation.
4. Process Chemistry Intermediate
Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH functions as a chiral, protected amino acid intermediate for process chemistry routes that require orthogonal protecting groups to manage reactivity during scale-up. The Fmoc carbamate and Boc carbamate provide predictable stability under coupling conditions and can be removed under controlled conditions to expose specific nucleophilic sites for sequential transformations. The heterocyclic piperazine substituent introduces a handle for controlled salt formation and for conversion into downstream functionalized intermediates used in fine chemical synthesis. The compound's defined stereochemistry and protected-group compatibility make it suitable for manufacturing-oriented synthesis planning where reproducible intermediate quality and controlled deprotection logic are required for subsequent peptide building block preparation or derivatization steps.
5. Analytical Standards Development
Fmoc-beta-(1-piperazinyl)-Ala(Boc)-OH is applicable to analytical research and method development because its protected structure provides distinct chromatographic and spectroscopic signatures for monitoring amino acid derivative synthesis and peptide coupling outcomes. The combination of Fmoc and Boc groups yields characteristic fragments in mass spectrometry and predictable behavior in reversed-phase chromatography, supporting identification of protected amino acid intermediates and their deprotected forms. The beta-(1-piperazinyl) side chain contributes ionizable features that can be leveraged for LC-MS detection and for establishing reference standards for side-chain integrity in peptide building block workflows. The compound can therefore serve as a chemical reference material for quality control of protected amino acid chemistry, peptide intermediate characterization, and verification of stereochemical retention in synthetic sequences.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More