Fmoc-Ala-Gln(Trt)-OH incorporates a protected glutamine side chain enabling selective deprotection during synthesis. Alanine contributes structural simplicity for backbone modeling. Researchers evaluate its performance in resin-bound coupling reactions. Applications include synthetic optimization, sequence extension, and controlled side-chain chemistry.
CAT No: R2525
CAS No:2411591-25-6
Synonyms/Alias:2411591-25-6;Fmoc--Ala-Gln(Trt)-OH;Fmoc-N2-(3-aminopropanoyl)-N5-trityl-L-glutamine;(S)-2-(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanamido)-5-oxo-5-(tritylamino)pentanoic acid;Fmoc-beta-Ala-Gln(Trt)-OH;Fmoc-|A-Ala-Gln(Trt)-OH;starbld0048825;MFCD31714902;CS-0439390;G87283;
Fmoc--Ala-Gln(Trt)-OH is a synthetic peptide building block featuring an N-terminal fluorenylmethyloxycarbonyl (Fmoc) protecting group on alanine and a side-chain trityl (Trt) protection on glutamine. As a bifunctionally protected dipeptide, it plays a pivotal role in solid-phase peptide synthesis (SPPS), enabling the efficient assembly of peptide sequences that incorporate both alanine and glutamine residues. Its design facilitates controlled coupling reactions and selective deprotection steps, which are essential for producing high-fidelity peptides in research and development settings. The compound's stability and compatibility with standard peptide synthesis protocols make it a valuable tool for a range of peptide-centric scientific investigations.
Peptide Synthesis: As a pre-assembled dipeptide, Fmoc--Ala-Gln(Trt)-OH is widely used in automated and manual SPPS workflows. Its incorporation streamlines the construction of longer peptide chains, particularly those containing consecutive alanine and glutamine residues. The Fmoc group protects the N-terminus during iterative coupling cycles, while the Trt group safeguards the glutamine side chain from undesired reactions, minimizing side-product formation and enhancing overall yield and purity of the target peptide.
Sequence Optimization: The use of protected dipeptide units such as Fmoc--Ala-Gln(Trt)-OH can significantly improve synthetic efficiency and sequence fidelity, particularly in challenging peptide regions prone to aggregation or racemization. By introducing pre-formed dipeptides, researchers can reduce the number of coupling steps and mitigate sequence-dependent synthesis difficulties, which is especially beneficial in the assembly of bioactive peptides, enzyme substrates, or peptide-based biomaterials.
Peptide Modification Studies: In research focused on the structural or functional modification of peptides, this protected dipeptide serves as a versatile intermediate. The orthogonal protection strategy allows for selective deprotection and subsequent functionalization of the glutamine side chain, enabling the introduction of post-synthetic modifications such as labeling, conjugation, or crosslinking. This facilitates the development of customized peptide probes and advanced molecular tools for biochemical assays.
Structure-Activity Relationship (SAR) Research: Fmoc--Ala-Gln(Trt)-OH is instrumental in the systematic exploration of peptide structure-activity relationships. By enabling the precise placement of alanine and glutamine within synthetic peptide libraries, it supports studies aimed at elucidating the roles of these residues in protein-protein interactions, enzyme recognition, or receptor binding. Such SAR investigations are critical for the rational design of novel peptides with improved biological or physicochemical properties.
Analytical Peptide Standards: The compound is also employed in the synthesis of custom peptide standards for analytical applications. Laboratories engaged in mass spectrometry, chromatography, or immunoassay development use peptides containing alanine-glutamine motifs to calibrate instruments, validate assay performance, or serve as internal controls. The high synthetic reliability afforded by protected dipeptide building blocks ensures the consistency and reproducibility required for these demanding analytical workflows.
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