Fmoc-D-Hse(Trt)-OH is a protected, non-proteinogenic amino acid derivative featuring the D-configured side chain of homoserine (Hse) bearing a trityl (Trt) ether protection on the side-chain hydroxyl, along with an N-terminal fluorenylmethoxycarbonyl (Fmoc) carbamate. The molecule contains an Fmoc-protected amino group and a carboxylic acid functionality, while the Trt group masks the hydroxyl to reduce chemoselectivity issues during peptide bond formation and to limit side reactions from the side-chain alcohol. In peptide chemistry and chemical biology workflows, it is used as a building block for stepwise incorporation of a hydroxyl-bearing amino acid residue under controlled protection patterns, supporting synthesis of modified peptides and subsequent deprotection and functionalization of the side-chain alcohol.
CAT No: CP25675
CAS No:257886-01-4
Synonyms/Alias:Fmoc-D-Hse(Trt)-OH;257886-01-4;Fmoc-D-Homoser(Trt)-OH;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(trityloxy)butanoic acid;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-trityloxybutanoic acid;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-(triphenylmethoxy)butanoic acid;DTXSID20585041;MFCD01631663;AKOS027251011;HY-W142085;AS-57086;DA-63517;CS-0201869;E70581;Fmoc-D-Homoser(Trt)-OH, >=98.0% (HPLC);N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-trityl-D-homoserine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-trityl-D-homoserine;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-O-(triphenylmethyl)-D-homoserine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(trityloxy)butanoicacid;
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-trityl-D-homoserine
Fmoc-D-Hse(Trt)-OH is a fluorenylmethoxycarbonyl (Fmoc) protected D-amino acid derivative featuring a side chain based on homoserine (Hse) functionality and a trityl (Trt) protected side-chain group. The molecule contains an Fmoc carbamate on the amino terminus, a carboxylic acid for C-terminal activation, and a stereogenic center that is fixed as the D configuration, supporting stereochemically defined peptide assembly. Trt protection on the side-chain heteroatom(s) moderates nucleophilicity during peptide coupling and can be removed under acidic deprotection conditions to reveal a reactive hydroxyl functionality for subsequent derivatization. The combination of orthogonal protection and a protected amino acid framework makes Fmoc-D-Hse(Trt)-OH suitable for controlled peptide building-block synthesis and downstream functionalization of the homoserine-derived side chain.
1. Peptide Synthesis
Fmoc-D-Hse(Trt)-OH is applied in solid-phase peptide synthesis and solution-phase peptide coupling where a D-configured amino acid building block is required. The Fmoc group enables base-mediated removal to expose the amino terminus for iterative coupling, while the carboxylic acid participates in standard peptide bond formation strategies. Trt protection on the side-chain functionality helps maintain chemoselectivity by suppressing undesired side reactions during coupling cycles and during orthogonal deprotection steps. Incorporation of this protected D-homoserine analog supports stereodefined peptide construction for structure-activity relationship studies and for generating peptide analogs with controlled side-chain reactivity.
2. Amino Acid Modification
Fmoc-D-Hse(Trt)-OH is used as a chiral intermediate for amino acid derivatization and side-chain functional group transformation. The protected side-chain group bearing Trt can be deprotected to reveal the corresponding hydroxyl functionality, enabling subsequent conversion to esters, ethers, or other oxygen-based motifs that modulate polarity and reactivity. The maintained D stereochemistry supports stereospecific downstream chemistry, including preparation of hydroxyl-functional peptidomimetics and stereochemically defined conjugation handles. The Fmoc-protected amino acid framework also supports sequential protection/deprotection logic when designing multi-step derivatization routes in fine chemical synthesis.
3. Bioconjugation Chemistry
Fmoc-D-Hse(Trt)-OH can be employed in bioconjugation workflows that require controlled presentation of a hydroxyl-bearing, stereodefined amino acid residue within peptide or linker scaffolds. The Fmoc group supports incorporation into peptide linkers that can later be deprotected and assembled into conjugates, while the carboxylic acid functionality enables formation of amide-linked fragments used in coupling to biomolecular targets. Trt-protected side-chain functionality helps prevent premature reactivity during linker synthesis, supporting cleaner downstream conjugation chemistry after side-chain deprotection. The D-homoserine stereocenter can be leveraged to tune conformational preferences and to generate defined conjugate structures for biochemical research and analytical characterization.
4. Peptidomimetics And SAR
Fmoc-D-Hse(Trt)-OH is suitable for peptidomimetic construction and structure-activity relationship studies where stereochemistry and side-chain oxygen chemistry influence molecular recognition. The D configuration and protected side-chain hydroxyl motif enable systematic variation of hydrogen-bonding patterns, polarity, and steric effects across peptide analog series. Fmoc compatibility supports rapid assembly of analog libraries, while Trt protection supports controlled unveiling of the side-chain functionality for late-stage modification. The resulting D-homoserine-containing scaffolds can be used to generate structurally consistent SAR panels and to support fragment-based molecular design efforts that require defined stereochemical inputs.
5. Pharmaceutical Manufacturing
Fmoc-D-Hse(Trt)-OH is relevant to pharmaceutical manufacturing contexts that involve peptide intermediate preparation and controlled protection-group handling for process chemistry. The orthogonal protection pattern, with Fmoc for base-labile amino deprotection and Trt for acid-labile side-chain deprotection, aligns with manufacturing workflows that require predictable deprotection sequencing and minimized side reactions during coupling. The carboxylic acid handle supports conversion into activated derivatives for peptide bond formation steps used to build defined intermediates and drug substance-related fragments. The stereochemically defined D-amino acid residue can be incorporated into manufacturing routes for peptide-based materials where stereochemical integrity and functional group timing are critical to downstream conversion and purification.
6. Analytical Research Standards
Fmoc-D-Hse(Trt)-OH is used in analytical research for preparing reference standards and for supporting method development in amino acid and peptide analysis. The defined D stereochemistry and protected functional groups provide a structurally unambiguous target for LC-MS, HPLC, or derivatization-based assays that monitor deprotection, coupling completeness, or side-chain transformation. Trt protection can help distinguish side-chain-reactive species from fully protected intermediates during analytical workflows that track orthogonal deprotection events. The Fmoc-tagged amino acid framework also supports preparation of peptide fragments and calibration materials that reflect realistic synthetic intermediates encountered during peptide building-block synthesis.
1. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment
5. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die
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