Fmoc-Ala-(Dmb)Gly-OH is a protected peptide building block featuring an N-terminal Fmoc-protected alanine linked to a glycine residue bearing a Dmb (4,4-dimethylbenzhydryl) side-chain protecting group, forming an amino acid derivative in a dipeptide-like format. The molecule contains a free C-terminal carboxylic acid and an Fmoc carbamate on the amino terminus, while the Dmb group protects the glycine amino functionality to control chemoselectivity during stepwise coupling and to reduce undesired side reactions. In peptide synthesis workflows, it functions as a substrate for sequential amide bond formation and as a protected intermediate for preparing longer peptides or peptide analogues with orthogonally protected amino components suitable for controlled deprotection strategies.
CAT No: CP26233
CAS No:1188402-17-6
Synonyms/Alias:Fmoc-Ala-(Dmb)Gly-OH;1188402-17-6;2-[(2,4-dimethoxyphenyl)methyl-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]acetic acid;(S)-2-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-N-(2,4-dimethoxybenzyl)propanamido)acetic acid;MFCD08064314;Fmoc-L-Ala-(Dmb)Gly-OH;AS-82335;FF111382;CS-0442203;N-((((9H-fluoren-9-yl)methoxy)carbonyl)-L-alanyl)-N-(2,4-dimethoxybenzyl)glycine;2-[(2S)-N-[(2,4-dimethoxyphenyl)methyl]-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanamido]acetic acid;
Fmoc-Ala-(Dmb)Gly-OH is a protected peptide building block featuring an Fmoc-protected alanine residue linked to a glycine bearing a Dmb (4,4-dimethylbenzyl) side-chain protecting group on the amino functionality, with a free carboxylic acid at the termini for downstream coupling. The structure combines a chiral alanine center with a protected amino acid motif, enabling stereochemically defined peptide bond formation under standard amide coupling conditions. The Fmoc group provides base-labile protection for the N-terminus, while the Dmb group is acid-labile and can be selectively removed to reveal an amine for orthogonal functionalization. The presence of both aromatic protecting group elements and a terminal carboxylic acid supports controlled reactivity across synthesis, purification, and subsequent derivatization steps.
1. Peptide Synthesis
Fmoc-Ala-(Dmb)Gly-OH serves as a two-residue peptide fragment for solid-phase peptide synthesis and solution-phase peptide assembly where orthogonal N-protection is required. The Fmoc group enables stepwise N-terminal deprotection and coupling, while the Dmb-protected glycine amine can remain masked to prevent premature branching or side reactions during chain elongation. The free carboxylic acid at the fragment end supports activation and coupling to the next amino acid building block, maintaining the alanine stereocenter contribution to sequence-defined conformations. The resulting peptide synthesis workflow can generate Ala-(Dmb)Gly-containing sequences that later undergo selective amine unmasking for further peptide modification or conjugation.
2. Side-Chain Functionalization
Fmoc-Ala-(Dmb)Gly-OH is suitable for amino acid derivatization strategies that require orthogonal deprotection to access a protected glycine amine after peptide assembly. The Dmb protecting group can be removed under conditions compatible with peptide frameworks to generate a primary amine handle for acylation, sulfonylation, carbamate formation, or attachment of linkers used in chemical biology. The Fmoc-protected alanine portion supports controlled exposure of reactive sites by maintaining N-protection during early-stage transformations. Downstream derivatives can be used to create site-specific functionalized peptides, enabling structure-encoded chemical modifications that preserve peptide backbone integrity and stereochemical definition.
3. Bioconjugation Chemistry
Fmoc-Ala-(Dmb)Gly-OH can function as a protected intermediate for preparing conjugatable peptide segments used in biomolecule labeling workflows. The terminal carboxylic acid and the orthogonally protected glycine amine enable staged coupling to activated esters or carboxamide-forming reagents, followed by selective deprotection to install conjugation moieties at a defined position. The aromatic protecting groups (Fmoc and Dmb) support purification by chromatographic behavior during synthesis and can be removed to expose reactive amines without disrupting the peptide backbone. The resulting amine-bearing peptide constructs are compatible with downstream attachment to carriers, probes, or affinity tags used for biochemical research and applied labeling.
4. SAR Studies
Fmoc-Ala-(Dmb)Gly-OH supports structure-activity relationship investigations by enabling the preparation of peptide analogs with controlled protecting-group patterns and sequence-defined modifications. The alanine stereocenter and the protected glycine amine allow systematic variation of side-chain chemistry at the glycine position while keeping the backbone composition fixed across analog libraries. The Fmoc strategy supports reproducible assembly of N-terminus-defined constructs, while Dmb unmasking provides a predictable point for introducing substituents that can modulate physicochemical properties such as polarity and hydrogen-bonding. Synthesized analogs can be used as defined chemical entities for comparative binding, stability, or mechanistic studies in medicinal chemistry and chemical biology contexts.
5. Pharmaceutical Manufacturing
Fmoc-Ala-(Dmb)Gly-OH is applicable to industrial peptide intermediate preparation where orthogonally protected residues are required for scalable and reproducible manufacturing routes. The Fmoc group provides base-labile control of N-terminal deprotection, supporting predictable coupling steps in automated peptide synthesis equipment, while the Dmb group offers an acid-labile handle for later-stage amine exposure. The fragment's free carboxylic acid supports incorporation into larger peptide sequences through standard activation chemistry, aligning with common process chemistry intermediate handling. The compound's protected architecture can be integrated into downstream purification and conversion steps to generate well-defined peptide materials or peptide-derived intermediates for specialty chemical production.
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