Fmoc-Gln(Dod)-OH is an Fmoc-protected glutamine derivative in which the side-chain amide of glutamine is modified with a DOD substituent, yielding a non-natural, sterically and electronically altered amino acid building block for peptide chemistry. The molecule contains an N-terminal fluorenylmethyloxycarbonyl (Fmoc) carbamate protecting group and a free carboxylic acid, while the side chain retains an amide functionality bearing the DOD modification, with stereochemistry consistent with the glutamine framework as implied by the name. In synthesis, it functions as a protected amino acid intermediate for stepwise incorporation into peptides via protected-amino-acid coupling strategies, and the side-chain modification supports structure-activity studies or chemical biology workflows that require glutamine analogues with altered reactivity or labeling handles.
CAT No: CP26204
CAS No:113534-17-1
Synonyms/Alias:Fmoc-Gln(Dod)-OH;113534-17-1;Nalpha-Fmoc-Ndelta-(4,4'-dimethoxybenzhydryl)-L-glutamine;C35H34N2O7;Fmoc-Gln(Mbh)-OH;47522_ALDRICH;SCHEMBL119478;47522_FLUKA;MolPort-003-934-146;ZINC4544831;AKOS015909024;AM002044;FT-0642774;I14-32968;N|A-Fmoc-N|A-(4,4invertedexclamationmarka-dimethoxybenzhydryl)-L-glutamine;(2S)-4-{[BIS(4-METHOXYPHENYL)METHYL]CARBAMOYL}-2-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}BUTANOICACID
Fmoc-Gln(Dod)-OH is an Fmoc-protected glutamine derivative in which the side-chain amide is masked as a DOD (dodecyl oxycarbonyl/alkoxycarbonyl-type) protected group, preserving the α-amino acid stereochemistry for peptide coupling. The molecule contains an Fmoc carbamate on the α-amine, a free α-carboxylic acid for C-terminal activation, and a protected side-chain amide that modulates polarity and suppresses undesired acylation during synthesis. The DOD-protected side chain can be selectively removed under conditions compatible with peptide assembly, enabling controlled exposure of the glutamine side-chain functionality for subsequent derivatization. The combination of orthogonal protection elements makes Fmoc-Gln(Dod)-OH suitable for stepwise construction of peptide building blocks and downstream intermediate preparation in both research and manufacturing contexts.
1. Peptide Synthesis
Fmoc-Gln(Dod)-OH supports solid-phase peptide synthesis workflows by providing an Fmoc-protected α-amino group for standard base-mediated deprotection and coupling. The free α-carboxylic acid enables activation and formation of a peptide bond while the DOD-masked side-chain amide reduces side reactions such as premature nucleophilic participation from the glutamine side chain. Orthogonal deprotection of the DOD group can be timed to reveal the side-chain amide for glutamine-specific chemistry after the peptide backbone is assembled. Downstream peptide analogs prepared from this protected glutamine building block can be used for studying amide-mediated hydrogen bonding patterns and for generating sequence-defined constructs in peptide science.
2. Side-Chain Functionalization
Fmoc-Gln(Dod)-OH serves as a protected amino acid intermediate for side-chain modification strategies that require controlled access to the glutamine amide. The DOD protection on the side-chain amide allows the compound to undergo peptide coupling or other derivatization steps without exposing a reactive nucleophile. After selective removal of the DOD group, the liberated side-chain amide can be employed for further transformations such as acylation, conjugation handle installation, or incorporation into peptidomimetic scaffolds that rely on side-chain hydrogen-bonding capacity. This protection/deprotection logic is directly relevant to amino acid derivatization and to generating functionalized peptide fragments for chemical biology and materials-facing conjugates.
3. Chemical Biology Probes
Fmoc-Gln(Dod)-OH can be applied in chemical biology research where glutamine-containing peptides or protein segments are needed as recognition elements or labeling substrates. The Fmoc-protected α-amino acid framework enables incorporation into defined peptide sequences, while the protected side-chain amide helps maintain chemoselectivity during synthesis of probe scaffolds. Controlled unmasking of the DOD group allows installation of functional reporters or affinity tags through glutamine side-chain chemistry, supporting downstream probe generation for mapping binding interfaces or monitoring molecular interactions. The resulting glutamine-bearing constructs can be used as research intermediates for studying structure-function relationships in peptide-mediated recognition.
4. Peptidomimetics And SAR Studies
Fmoc-Gln(Dod)-OH is suitable for peptidomimetic construction and structure-activity relationship studies that require reproducible glutamine-like side-chain presentation. The stereochemically defined α-amino acid core and the protected side-chain amide enable sequence-accurate assembly of peptide analogs where side-chain orientation and hydrogen-bonding contribute to binding patterns. The orthogonal protection scheme supports iterative synthesis of analog libraries, including late-stage side-chain unmasking for systematic functional variation. Generated analogs can then be used as defined chemical entities in SAR workflows to correlate side-chain modifications with changes in molecular recognition behavior.
5. Pharmaceutical Intermediate Preparation
Fmoc-Gln(Dod)-OH can function as a process-relevant protected amino acid intermediate in fine chemical synthesis routes that produce glutamine-containing peptide fragments for further manufacturing steps. The Fmoc carbamate and DOD-masked side-chain amide provide protection of both nucleophilic sites during controlled activation and coupling operations, reducing impurity formation from uncontrolled acylation or side-chain participation. The presence of a free α-carboxylic acid supports conversion into activated derivatives or coupling-ready forms within peptide-building supply chains. Downstream, the compound can be used to manufacture sequence-defined intermediates that feed into larger peptide or peptidomimetic production strategies used in industrial chemical manufacturing.
6. Analytical Standards Development
Fmoc-Gln(Dod)-OH is applicable to analytical research and method development where protected amino acid standards or peptide coupling controls are required. The distinct combination of Fmoc and DOD protection yields characteristic chromatographic and spectrometric signatures that can support identification and quantification of glutamine-containing building blocks during peptide assembly. The α-carboxylic acid and protected side-chain amide enable preparation of reference materials for monitoring coupling efficiency, deprotection completeness, and side-product formation in protected amino acid chemistry. The resulting standards can be employed in QA-oriented analytical workflows for peptide synthesis process development and for verifying intermediate integrity in applied amino acid derivative manufacturing.
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