FA-Ala-OSu

FA-Ala-OSu is a formyl-activated L-alanine derivative in which the amino acid is presented as a carboxylate activated as an N-hydroxysuccinimide (OSu) ester, enabling acyl transfer chemistry under peptide-synthesis conditions. The molecule contains a stereogenic center at the alanine alpha-carbon, an amide-forming amino functionality, and a formyl group that can influence chemoselectivity during coupling or subsequent deprotection workflows. The OSu ester bears an electrophilic carbonyl that can react with nucleophiles such as amines to form new amide bonds, while the succinimide leaving group supports efficient peptide coupling strategies. The presence of the formyl substituent and the protected/activated carboxyl state makes FA-Ala-OSu a chiral amino acid intermediate suitable for downstream conversion into protected or incorporated alanine units in peptide and peptidomimetic syntheses.

1. Peptide Coupling Chemistry

FA-Ala-OSu is used in peptide synthesis workflows where OSu ester activation supports amide bond formation with incoming amines, including protected amino acid side-chain nucleophiles and resin-bound or solution-phase amino components. The alanine backbone provides a stereochemically defined alpha-carbon, while the activated carboxyl group participates directly in coupling without requiring pre-activation by carbodiimides. The formyl substituent can be leveraged to tune chemoselectivity and compatibility with orthogonal protecting-group strategies during stepwise assembly of peptide building blocks. Downstream, the resulting amide-linked products can serve as intermediates for further elongation, cyclization, or fragment ligation in synthetic peptide chemistry and peptide analog construction.

2. Bioconjugation Intermediates

FA-Ala-OSu is applicable to chemical biology and bioconjugation processes that require controlled acylation of amine-containing biomolecules or labeling handles. The OSu ester functionality reacts with primary amines to generate stable amide linkages, making the compound suitable for preparing alanine-derived linkers, peptide-protein conjugation precursors, or attachment motifs for biomolecule labeling. The defined L-configuration at the alanine center can be relevant when stereochemical integrity of the amino acid motif is needed for recognition in structure-function studies. The formyl/activated-carboxyl architecture enables conversion into amide-bearing conjugates that can be further processed into multivalent constructs or used as defined acylation reagents in applied biochemical research.

3. Protected Amino Acid Synthesis

FA-Ala-OSu is used as a chiral amino acid intermediate for constructing alanine-containing protected derivatives and for integrating alanine units into larger synthetic sequences. The OSu ester provides a handle for rapid transformation into amide-linked intermediates that can later be carried through protection/deprotection cycles, including conversion to peptide-grade carboxyl equivalents after nucleophile capture. The stereogenic center allows consistent incorporation of L-alanine stereochemistry into downstream protected amino acid derivatives and peptide building blocks, supporting stereocontrolled synthesis. The formyl group can be incorporated into synthetic logic for orthogonal compatibility, enabling stepwise assembly of intermediates that feed into protected amino acid chemistry and peptidomimetic construction.

4. Process Chemistry Intermediate

FA-Ala-OSu is suitable for process chemistry intermediate preparation where activated amino acid esters are used to streamline coupling steps in fine chemical manufacturing. The OSu ester activation mode supports scalable acyl transfer to nucleophiles, which can reduce reliance on separate coupling reagent systems and can simplify downstream purification logic relative to less activated carboxyl derivatives. The compound's defined functional group set, including the electrophilic ester carbonyl and the stereochemically fixed alanine core, supports reproducible formation of amide intermediates that can be carried into subsequent synthesis stages. The resulting amide-linked products can serve as controlled intermediates for specialty chemical production, including peptide fragment manufacture and industrial preparation of amino acid-based building blocks.

5. Analytical Standards And SAR Tools

FA-Ala-OSu is employed in analytical research and structure-activity relationship studies that require defined alanine-containing acylated motifs as reference compounds or synthetic probes. The OSu ester can be used to generate labeled or derivatized amide products with predictable connectivity to amine nucleophiles, supporting method development for LC-MS, HPLC, and MS/MS characterization of peptide fragments and coupling outcomes. The stereochemically defined L-alanine unit helps maintain structural fidelity when comparing analogs in SAR workflows or when validating synthetic identity of alanine-incorporated intermediates. The formyl/amide framework enables preparation of well-characterized derivatives that can function as analytical standards, impurity mapping targets, or scaffold elements in peptide and peptidomimetic SAR investigations.

1. The effect of B-type allatostatin neuropeptides on crosstalk between the insect immune response and cold tolerance

2. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

3. Implications of ligand-receptor binding kinetics on GLP-1R signalling

4. Cationic cell-penetrating peptides are potent furin inhibitors

5. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum