Fmoc-D-MeAla-OH is an Fmoc-protected, D-configured amino acid derivative featuring a 2-amino acid backbone and a side chain bearing a methyl substituent (MeAla), classifiable as a substituted alanine analog used in peptide chemistry. The molecule contains a free carboxylic acid and an Fmoc carbamate that masks the amino group, enabling controlled chemoselective deprotection during stepwise assembly while the D stereocenter is retained from the D-MeAla configuration. In synthesis and chemical biology workflows, this protected amino acid is employed as a building block for incorporating the D-methylalanine residue into peptides and peptide-related intermediates, including isotopically or structurally defined analogs for structure-activity and labeling studies.
CAT No: CP25338
CAS No:138774-92-2
Synonyms/Alias:138774-92-2;Fmoc-N-Me-D-Ala-OH;N-Fmoc-N-methyl-D-alanine;Fmoc-D-MeAla-OH;Fmoc-N-methyl-D-alanine;Fmoc-Nalpha-methyl-D-alanine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)propanoicacid;(2R)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]propanoicacid;AmbotzFAA1332;AC1LEMGW;47346_ALDRICH;SCHEMBL956106;47346_FLUKA;CTK7I3537;ZINC57598;MolPort-003-934-077;AKOS015837189;RTR-062393;VA50384;AJ-09744;AK-45723;AN-31769;AB0019633;TR-062393;FT-0629887
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-Methyl-D-alanine
Fmoc-D-MeAla-OH is a D-configured N-Fmoc-protected amino acid bearing a methyl-substituted alanine side chain (MeAla), providing a stereochemically defined chiral center for controlled peptide incorporation. The structure combines an Fmoc carbamate on the amino group with a free carboxylic acid, enabling orthogonal handling during solid-phase peptide synthesis and subsequent fragment coupling. The additional methyl substituent on the side chain modulates steric profile and hydrophobic character relative to alanine, which can influence conformational preferences in peptide analogs. The compound's protected amine and unprotected acid functionality support standard peptide chemistry transformations while maintaining compatibility with common protecting-group strategies.
1. Peptide Synthesis
Fmoc-D-MeAla-OH is used as a D-amino acid building block in peptide synthesis workflows where Fmoc-based N-protection and a free carboxyl group are required for stepwise chain assembly. The Fmoc group supports base-labile deprotection, while the carboxylic acid participates in peptide coupling to form stable amide bonds at the growing peptide termini. The D-stereochemistry and methylated side chain can be incorporated to tune local backbone geometry, steric bulk, and hydrophobic interactions in peptide sequences and peptide fragments. Downstream peptide construction benefits from predictable incorporation of this chiral residue into protected peptide intermediates and final peptide products.
2. Peptidomimetics Design
Fmoc-D-MeAla-OH serves in peptidomimetic construction and molecular design programs that require stereodefined, side-chain-modified amino acid units. The methyl-substituted MeAla side chain provides a compact hydrophobic group that can be leveraged to modulate conformational bias, backbone packing, and solvent exposure in peptide analog scaffolds. The D configuration enables access to mirror-image residue patterns that are frequently used to probe stereochemical effects on binding or stability in structure-activity relationship studies. The Fmoc-protected format supports efficient synthesis of analog libraries where subsequent functional group elaboration can be performed on other residues while preserving the incorporated D-MeAla motif.
3. SAR Studies
Fmoc-D-MeAla-OH is applied in structure-activity relationship studies for generating stereochemically defined peptide variants and position-specific analogs. The combination of an Fmoc-protected amine and a free carboxylic acid allows consistent peptide coupling at the residue level, supporting systematic variation of sequence context while keeping the D-MeAla stereocenter intact. The side-chain methyl substitution can be used to evaluate steric and hydrophobic contributions at specific positions, including in constrained or helix-influencing peptide designs. The resulting analogs can be used as research materials for comparative binding and stability investigations, and the residue's protected nature supports parallel synthesis of SAR panels.
4. Protein Engineering
Fmoc-D-MeAla-OH can be employed in protein engineering and chemical protein modification contexts where D-amino acid incorporation or peptide segment assembly is used to alter local structure. The Fmoc-protected amino acid format enables preparation of protected peptide segments that can be assembled into larger constructs, including chemically synthesized domains or interface peptides used to study protein interactions. The D configuration and methylated side chain can influence secondary-structure propensity and resistance to proteolysis in peptide-derived components, supporting experimental designs that assess how stereochemistry and side-chain bulk affect molecular recognition. The free carboxylic acid and orthogonal protection strategy facilitate coupling into defined sequences for downstream conjugation or fragment-based assembly.
5. Pharmaceutical Manufacturing
Fmoc-D-MeAla-OH is suitable for pharmaceutical manufacturing workflows that involve the production of Fmoc-based peptide intermediates and controlled stereochemical building blocks. The Fmoc-protected amine supports standardized deprotection and coupling operations during peptide manufacture, while the free acid enables consistent formation of amide linkages with activated carboxyl partners. The D-MeAla residue can be incorporated into peptide drug substance candidates or peptide-based intermediates to generate defined stereochemical sequences used in process development and analytical method qualification. The compound's stable protected functionality makes it compatible with industrial peptide synthesis logistics, including preparation of protected amino acid stocks and intermediate peptide fragments.
6. Analytical Research
Fmoc-D-MeAla-OH is used in analytical research settings to prepare labeled or reference peptide standards that contain a defined D-MeAla residue. The Fmoc protection strategy enables incorporation into peptides with controlled N-terminal protection patterns, supporting reproducible chromatographic behavior and mass spectrometric signatures for method development. The methylated side chain and D stereochemistry provide distinguishable structural features that can help resolve isomeric or closely related peptide standards during LC-MS and related analytical workflows. The compound's role as a chiral, residue-level building block supports downstream generation of well-defined analytical materials for monitoring synthesis, purity profiling, and structural verification of peptide products.
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