Fmoc-alpha-Me-D-Orn(Boc)-OH is a protected, non-proteinogenic amino acid derivative based on ornithine bearing an Nα-(9H-fluoren-9-ylmethoxycarbonyl) (Fmoc) protecting group, an α-methyl substitution, and D stereochemistry at the amino acid center. The molecule contains a free carboxylic acid and an amino acid side chain with a Boc-protected terminal amine, so its functional groups are organized for controlled chemoselectivity during stepwise peptide assembly. In solid-phase or solution-phase peptide synthesis and related chemical biology workflows, the Fmoc and Boc groups provide orthogonal protection of the α-amino and side-chain amino functionalities, while the α-methyl and D-configuration support incorporation into peptides for structure-activity, conformational, or labeling studies.
CAT No: CP25457
CAS No:171860-40-5
Synonyms/Alias:171860-40-5;Fmoc-Alpha-Me-D-Orn(Boc)-OH;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;(R)-Na-Fmoc-NW-Boc-alpha-Methylornithine;MFCD17019259;FMoc--Me-D-Orn(Boc)-OH;Fmoc-beta-Me-D-Orn(Boc)-OH;AKOS030212535;AT30755;(2r)-5-(tert-butoxycarbonylamino)-2-(9h-fluoren-9-ylmethoxycarbon Ylamino)-2-methyl-pentanoic Acid;(R)-Nomega-(t-Butoxycarbonyl)-Nalpha-(9-fluorenylmethoxycarbonyl)-alpha-methylornithin;(2R)-2-((((9H-FLUOREN-9-YL)METHOXY)CARBONYL)AMINO)-5-((TERT-BUTOXYCARBONYL)AMINO)-2-METHYLPENTANOIC ACID;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid;691-378-1;
Chemical Name:(R)-N-alpha-(9-Fluorenylmethyloxycarbonyl)-C-alpha-methyl-N-delta-t-butyloxycarbonyl-ornithine
Fmoc-alpha-Me-D-Orn(Boc)-OH is an Fmoc-protected, alpha-methylated D-ornithine derivative bearing a Boc-protected side-chain amine, providing two orthogonal nitrogen-protection elements for stepwise peptide assembly. The molecule combines a chiral alpha-center with a D-configuration at the amino acid backbone, while the side chain presents a protected primary amine suitable for later deprotection and functional group installation. The Fmoc group enables base-labile removal under standard peptide synthesis conditions, whereas the Boc group provides acid-labile control of the side-chain functionality. The presence of an amino acid ester-free carboxylic acid (as a free acid) and the sterically defined alpha-methyl substitution influence coupling behavior, conformational preferences, and downstream derivatization pathways in both research and manufacturing workflows.
1. Peptide Synthesis
Fmoc-alpha-Me-D-Orn(Boc)-OH is used in peptide building block preparation for solid-phase peptide synthesis where orthogonal N-protection is required for controlled N-alkylation or side-chain elaboration. The Fmoc-protected alpha-amine supports reliable coupling to growing peptide chains, while the Boc-protected side-chain amine preserves the ornithine functionality during chain elongation. The D-stereochemistry and alpha-methyl substitution can be applied to generate peptides with defined backbone stereochemical patterns and altered local conformations, supporting peptide analog construction and sequence-specific studies. The free carboxylic acid functionality is compatible with common amino acid activation strategies used in peptide coupling chemistry, enabling stepwise synthesis of protected intermediates and final peptide products.
2. Peptidomimetics And SAR
Fmoc-alpha-Me-D-Orn(Boc)-OH is applied in peptidomimetic construction and structure-activity relationship studies where ornithine-derived side-chain spacing and amine reactivity are key design parameters. The protected side-chain amine allows installation of substituents after peptide assembly, supporting generation of constrained or substituted analogs that probe binding-site tolerance to stereochemistry and steric bulk. The alpha-methyl and D-configuration can be leveraged to modulate backbone rigidity and intramolecular hydrogen bonding propensity, which may influence structure-function relationships in peptide-like scaffolds. The resulting derivatives can feed medicinal chemistry campaigns by providing chemically defined, synthesis-ready building blocks for SAR libraries and fragment-to-lead optimization workflows.
3. Side-Chain Functionalization
Fmoc-alpha-Me-D-Orn(Boc)-OH supports side-chain functionalization strategies in chemical biology and synthetic organic chemistry by providing a protected primary amine handle on the ornithine side chain. Boc protection enables selective deprotection after peptide assembly or intermediate synthesis, allowing subsequent conversion to amide, sulfonamide, urea, carbamate, or alkylated derivatives depending on the chosen coupling partners. The orthogonal Fmoc/Boc protection pattern helps manage chemoselectivity when introducing additional functional groups that may otherwise react during peptide coupling steps. The alpha-methylated D-amino acid framework can further serve as a stereochemically defined scaffold for preparing functionalized amino acid derivatives and downstream conjugation-ready intermediates.
4. Bioconjugation Chemistry
Fmoc-alpha-Me-D-Orn(Boc)-OH is suitable for bioconjugation workflows that require incorporation of a protected amine-containing amino acid motif into peptides or peptide-like linkers prior to conjugation. The side-chain Boc group provides a protected nucleophile that can be unmasked under controlled conditions to enable attachment to activated esters, isothiocyanates, aldehyde-derived linkers, or other electrophiles used in conjugation chemistry. The Fmoc group facilitates incorporation into peptide carriers or targeting sequences, while the D-configuration and alpha-methyl substitution can help tune stability and conformational behavior of the conjugate scaffold. The resulting functionalized constructs can be used to generate defined biomolecule conjugates for biochemical assays, molecular recognition studies, and labeling strategies that depend on precise linker architecture.
5. Process Chemistry Intermediates
Fmoc-alpha-Me-D-Orn(Boc)-OH is used as a chiral amino acid intermediate in fine chemical synthesis and process chemistry where orthogonally protected nitrogen functionality supports scalable, stepwise manufacturing routes. The Fmoc group and Boc-protected side-chain amine are designed for sequential deprotection and derivatization logic, enabling controlled progression from protected building block to elaborated peptide or functionalized amino acid derivatives. The stereodefined D-backbone and alpha-methyl substitution support reproducible stereochemical outcomes across synthetic batches, which is relevant for consistent intermediate quality in industrial peptide supply chains. The compound's protected, amino acid-compatible structure allows integration into established peptide building block manufacturing practices and downstream conversion to specialized ornithine-based intermediates for specialty chemical production.
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