Fmoc-L-Pro(4-N3)-OH (2S,4S)

Fmoc-L-Pro(4-N3)-OH (2S,4S) is an Fmoc-protected, stereodefined proline derivative bearing an azide substituent at the 4-position, corresponding to the (2S,4S) configuration of the pyrrolidine ring. The molecule combines a chiral amino acid backbone with a protected α-amino group (Fmoc carbamate) and a carboxylic acid handle suitable for amide bond formation in peptide chemistry. The side-chain azide provides a chemically orthogonal functional group for post-coupling derivatization while remaining stable under many peptide synthesis conditions. The azide-bearing, N-Fmoc amino acid thus functions as a chiral building block and a downstream clickable handle for constructing functional peptide analogs and research intermediates.

1. Peptide Synthesis

Fmoc-L-Pro(4-N3)-OH (2S,4S) is used in solid-phase peptide synthesis and related protected amino acid strategies to introduce an azide-functionalized proline residue into peptide chains. The Fmoc carbamate protects the α-amine during coupling and can be removed under standard deprotection conditions to enable sequential elongation, while the carboxylic acid participates in peptide coupling chemistry. The (2S,4S) stereochemistry preserves the conformational and stereoelectronic properties associated with proline, supporting consistent structure in peptide scaffolds. The side-chain azide enables later functionalization without altering the backbone, supporting the preparation of azide-tagged peptides for downstream conjugation and library synthesis in biochemical research.

2. Bioconjugation Chemistry

Fmoc-L-Pro(4-N3)-OH (2S,4S) is applied as an azide-bearing amino acid building block for bioconjugation workflows that require orthogonal functional handles on peptides and peptide-derived biomolecules. The stable N-Fmoc protection supports controlled incorporation into peptide constructs, while the side-chain azide can be transformed into conjugatable motifs through azide-reactive chemistries after peptide assembly. The chiral proline residue can influence local conformation and presentation of the functional group, which can be relevant for molecular recognition studies and labeled biomolecule generation. Downstream derivatization of the azide enables construction of functional peptide conjugates used in chemical biology, biomolecule labeling, and analytical probe preparation.

3. Peptidomimetics And SAR Studies

Fmoc-L-Pro(4-N3)-OH (2S,4S) serves in peptidomimetic and SAR-oriented synthesis where a stereodefined proline unit bearing a reactive azide side chain supports systematic scaffold modification. The azide substituent provides a functional "switch" for generating analogs through controlled side-chain transformations, enabling structure-activity relationship studies that correlate side-chain chemistry with binding or activity readouts in vitro. The Fmoc-protected amino acid format supports incorporation into constrained peptide-like frameworks, including proline-rich motifs and turn-forming sequences. The resulting azide-containing intermediates can be further converted into diverse functional groups, supporting iterative medicinal chemistry and molecular design campaigns focused on structure-function mapping.

4. Chemical Biology Probes

Fmoc-L-Pro(4-N3)-OH (2S,4S) is utilized for chemical biology probe construction where an azide-bearing proline residue enables selective labeling or attachment of reporter groups to peptide targets. The orthogonal azide functionality allows post-synthetic modification of assembled peptides, while the Fmoc-protected α-amine ensures compatibility with peptide coupling and stepwise synthesis. The (2S,4S) stereochemistry provides reproducible stereochemical context, which can be important for probe behavior related to peptide conformation and target engagement. The azide handle supports generation of labeled peptides and probe intermediates for mechanistic studies, mapping experiments, and analytical investigations requiring controlled functional group placement.

5. Process Chemistry Intermediate

Fmoc-L-Pro(4-N3)-OH (2S,4S) is suitable as a manufacturing-oriented intermediate for producing azide-functionalized amino acid derivatives and peptide building blocks used across fine chemical and pharmaceutical intermediate supply chains. The Fmoc protection strategy supports robust handling during synthesis and downstream coupling operations, while the carboxylic acid group enables conversion into activated derivatives for peptide coupling in controlled process steps. The side-chain azide provides a single, well-defined reactive site that can be carried through peptide assembly and later transformed into process-compatible functional groups for further manufacturing. The stereodefined (2S,4S) configuration supports reproducibility in chiral amino acid intermediate preparation and enables consistent downstream synthesis of azide-tagged peptide analogs for research and industrial chemical production.

1. Emu oil in combination with other active ingredients for treating skin imperfections

2. Quantitative Analysis of Ligands Effects on Bioefficacy of Nanoemulsion encapsulating Depigmenting Active

3. GLP-1, exendin-4 and C-peptide regulate pancreatic islet microcirculation, insulin secretion and glucose tolerance in rats

4. Glucagonlike peptide 2 analogue teduglutide: stimulation of proliferation but reduction of differentiation in human Caco-2 intestinal epithelial cells

5. Crystal Structure of BamB from Pseudomonas aeruginosa and Functional Evaluation of Its Conserved Structural Features