Fmoc-L-Homocitrulline is an Fmoc-protected, L-configured non-proteinogenic amino acid derivative featuring a homocitrulline backbone with an additional methylene relative to citrulline and a side chain bearing a urea-like functionality. The molecule contains an N-terminal 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) protecting group on the amino group while retaining the free carboxyl group, and the side chain provides carbonyl-containing hydrogen-bonding and polar interactions that can influence peptide conformation and solubility. Fmoc-L-Homocitrulline is used as a building block for stepwise peptide synthesis and structure-activity or chemical biology studies where a urea-containing, non-proteinogenic residue is incorporated to probe hydrogen-bonding patterns and backbone/side-chain effects.
CAT No: CP06206
CAS No:201485-17-8
Synonyms/Alias:201485-17-8;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-ureidohexanoicacid;C22H25N3O5;Fmoc-Hcit-OH;Fmoc-L-homocitrulline;AmbotzFAA1383;SCHEMBL4882849;MolPort-008-267-651;ZINC2560801;0339AB;AKOS016010491;AJ-40655;AK117094;KB-210834
Fmoc-L-Homocitrulline is an Fmoc-protected L-homocitrulline amino acid derivative featuring the stereodefined α-amino acid backbone of L-configuration and a side chain bearing a urea-like functionality derived from the citrulline/homocitrulline motif. The molecule combines a carbamate-protected nitrogen (Fmoc) with a free carboxylic acid and an additional strongly polar, hydrogen-bonding capable side-chain group that can participate in nucleophilic and acyl-transfer chemistry under peptide-synthesis compatible conditions. The presence of the chiral center at the α-position and the conformationally influential side-chain functionality support controlled incorporation into peptide sequences and subsequent side-chain transformations after deprotection. The Fmoc/acid-protected pattern positions this compound as a practical chiral intermediate for protected amino acid synthesis, peptide building block preparation, and downstream derivatization in synthetic organic and biochemical research workflows.
1. Peptide Synthesis
Fmoc-L-Homocitrulline is used in peptide synthesis workflows where the Fmoc carbamate enables standard N-terminal protection and orthogonal deprotection strategies for stepwise chain assembly. The α-carboxylic acid supports peptide coupling chemistry, while the side-chain urea-like functionality can be maintained during assembly or selectively modified after Fmoc removal depending on the protecting-group scheme. Incorporation of the L-configured residue supports stereochemically defined backbone geometry and can influence local hydrogen-bonding patterns in the growing peptide. The resulting peptidic products serve as sequence-defined analogs for studying amino acid substitution effects and for constructing urea-rich motifs compatible with further functionalization.
2. Peptidomimetics And SAR
Fmoc-L-Homocitrulline is applied in peptidomimetic construction and structure-activity relationship studies where the side-chain polar functionality helps reproduce key recognition elements found in urea-containing pharmacophores. The Fmoc-protected amino acid format supports rapid generation of analog libraries by enabling controlled coupling at the amino acid level, followed by side-chain deprotection or functional group conversion to tune hydrogen-bonding capacity and polarity. The stereodefined L-homocitrulline center helps preserve conformational preferences relevant to molecular recognition models and SAR mapping. Downstream derivatives prepared from this residue can be used as research-grade scaffolds for evaluating how amino acid substitutions alter binding-relevant physicochemical properties.
3. Chemical Biology Conjugation
Fmoc-L-Homocitrulline is suitable for chemical biology applications that require incorporation of a polar, hydrogen-bonding side chain into peptide or protein-modifying constructs. The protected amino acid derivative can be assembled into peptides bearing defined reactive handles, where subsequent deprotection and side-chain chemistry can enable conjugation strategies such as attaching linkers, probes, or affinity tags through controlled functional group transformations. The combination of Fmoc protection and a side-chain capable of participating in targeted derivatization supports reproducible synthetic routes to labeled biomolecule fragments. The resulting conjugation-ready intermediates can be employed to generate sequence-defined chemical tools for studying biomolecular interactions and post-synthetic modification behavior.
4. Side-Chain Functionalization
Fmoc-L-Homocitrulline is used for side-chain functionalization routes in synthetic organic chemistry where the urea-like functionality provides a reactive platform for controlled derivatization. The Fmoc-protected nitrogen allows selective manipulation of the side chain after N-deprotection, enabling conversion into alternative carbonyl-containing or substituted urea derivatives while retaining the stereodefined amino acid skeleton. The free carboxylic acid can also be transformed into activated esters or coupling-ready derivatives for further downstream assembly into larger frameworks. This makes the compound a practical chiral amino acid intermediate for preparing functionalized derivatives used in fine chemical synthesis and in the construction of polar, hydrogen-bonding-rich molecular architectures.
5. Pharmaceutical Intermediate Preparation
Fmoc-L-Homocitrulline is applied as a chiral intermediate for pharmaceutical intermediate preparation where Fmoc protection supports scalable, protected amino acid synthesis and controlled handling of the α-amino functionality. The defined L-stereochemistry and the presence of a carboxylic acid facilitate conversion into activated intermediates for subsequent coupling steps in medicinal chemistry and process chemistry. The side-chain urea-like group can be carried through protected-manufacturing sequences and later converted into downstream structures that retain polar interaction motifs. The compound can therefore serve as a structured feedstock for manufacturing route design toward urea-containing peptide-like intermediates and related heteroatom-rich scaffolds used in applied chemical development.
6. Analytical Research Standards
Fmoc-L-Homocitrulline is used in analytical research as a reference building block for method development involving amino acid derivatives, protected peptide fragments, and urea-containing motifs. The Fmoc group provides a characteristic chromatographic and mass spectrometric signature, while the L-homocitrulline backbone and polar side chain support reproducible fragmentation patterns that can aid in identification of related analytes. The compound's defined stereochemistry enables stereospecific comparisons in workflows that distinguish L- from non-L residues or monitor derivatization completeness in protected amino acid chemistry. Analytical standards derived from this residue can be employed to support characterization of peptide coupling outcomes, side-chain conversion processes, and quality control of amino acid-based intermediates.
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