Fmoc-L-beta-HGln(Trt)-OH

Fmoc-L-beta-HGln(Trt)-OH is an Fmoc-protected, stereodefined glutamine-derived amino acid building block featuring an L-configuration at the alpha stereocenter and a side-chain amide functionality corresponding to the β-hydroxylated glutamine framework. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) carbamate that supports controlled peptide coupling under standard Fmoc deprotection conditions, while the side-chain amide is masked as a Trt-protected group to manage hydrogen-bonding and minimize undesired side reactions during chain assembly. The presence of a β-hydroxylated motif introduces an additional oxygen-bearing stereochemical element that can participate in selective derivatization, while the overall protected architecture modulates polarity and solubility for synthetic handling. The Trt group and the Fmoc carbamate create orthogonal protection behavior that can be exploited to tune deprotection order, enabling downstream conversion into functional peptide analogs and biochemical research intermediates.

1. Peptide Synthesis

Fmoc-L-beta-HGln(Trt)-OH is applied in solid-phase peptide synthesis and solution-phase peptide coupling workflows where orthogonal N- and side-chain protection is required for incorporating a β-hydroxylated glutamine residue. The Fmoc carbamate on the amino terminus enables iterative peptide bond formation after base-mediated Fmoc removal, while the Trt-protected side-chain functionality helps suppress side reactions and improves coupling reliability for amide-bearing residues. The β-hydroxy element can influence local conformation and hydrogen-bond networks in the growing peptide, supporting the construction of structurally defined peptide scaffolds for biochemical interrogation. The resulting protected amino acid derivative can be carried through standard deprotection sequences to furnish peptides bearing a glutamine-like side chain with controlled functional group presentation.

2. Chemical Biology

Fmoc-L-beta-HGln(Trt)-OH is suitable for chemical biology research that requires site-specific incorporation of a β-hydroxylated glutamine analog into peptide probes and protein-interaction studies. The combination of an amide-containing side chain and a stereodefined β-hydroxyl group supports formation of characteristic polar interactions, enabling the design of molecular recognition elements that mimic or modulate native hydrogen-bonding patterns. Trt protection can be leveraged to keep the side-chain from interfering during probe synthesis and subsequent conjugation steps, while Fmoc compatibility supports integration into peptide-based labeling constructs. Downstream, deprotected peptides prepared from this building block can serve as substrates, inhibitors, or binding probes in assays that interrogate recognition motifs at the amino acid level.

3. Peptidomimetics And SAR

Fmoc-L-beta-HGln(Trt)-OH can be employed in peptidomimetic and structure-activity relationship studies where controlled stereochemistry and side-chain functionality are used to tune binding conformations. The protected amide side chain and the β-hydroxyl stereocenter provide handles for hydrogen-bond donor/acceptor patterning, which can be systematically varied through deprotection and subsequent functional group transformations. Trt protection supports late-stage unveiling of the side-chain for scaffold diversification, while Fmoc removal enables assembly of analog series with consistent N-terminal architecture. Peptides and peptidomimetic fragments derived from this amino acid building block can be used to generate SAR libraries that map how β-hydroxylated glutamine-like features influence molecular recognition.

4. Bioconjugation Chemistry

Fmoc-L-beta-HGln(Trt)-OH is applicable to bioconjugation strategies that rely on peptide intermediates bearing defined polar functional groups for controlled coupling to biomolecular targets. The Fmoc-protected amino group allows synthesis of peptide segments that can be deprotected to expose reactive termini for conjugation chemistries, while Trt-protected side-chain functionality helps maintain stability during conjugate assembly. The β-hydroxyl group can serve as a site for further derivatization, including transformations that introduce linkers or reactive groups while preserving stereochemical fidelity from the chiral building block. Conjugates prepared via peptides incorporating this residue can be used for biomolecule labeling, affinity reagents, and mechanistic studies of protein-ligand interactions.

5. Pharmaceutical Intermediate Preparation

Fmoc-L-beta-HGln(Trt)-OH is relevant to pharmaceutical intermediate preparation for peptide-based or peptide-derived manufacturing routes that require protected chiral amino acid inputs. The Fmoc carbamate provides a robust N-protection strategy compatible with scalable peptide coupling and controlled deprotection logic, while Trt protection on the side chain supports handling of polar glutamine-like motifs without excessive side reactivity. The β-hydroxylated glutamine framework can be carried into downstream intermediate formation for larger peptide intermediates, enabling consistent stereochemical delivery into final active or pre-active peptide structures. Process chemistry workflows can incorporate this protected amino acid derivative as a defined building block for producing protected peptide fragments used in specialty chemical production and applied peptide synthesis.

6. Process Chemistry And Fine Chemical Synthesis

Fmoc-L-beta-HGln(Trt)-OH serves as a chiral amino acid intermediate for fine chemical synthesis where orthogonal protecting groups enable stepwise conversion into functional derivatives. The combination of Fmoc protection and Trt side-chain protection supports controlled deprotection order, which is valuable when designing manufacturing sequences that minimize impurity formation from reactive amide/oxygen functionalities. The stereodefined β-hydroxyl center and glutamine-like side chain can be retained through protected stages, allowing downstream conversion into deprotected amino acid residues, peptide fragments, or chemically modified analogs. The compound's protected architecture aligns with industrially practical peptide-building-block supply for research-grade and process-oriented synthesis of amino acid-derived intermediates.

1. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

2. Relatedness of antibodies to peptides containing homocitrulline or citrulline in patients with rheumatoid arthritis

3. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis

4. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

5. Zeta-potential-changing nanoparticles conjugated with cell-penetrating peptides for enhanced transfection efficiency