(S)-N-Fmoc-2-(6'-octenyl)glycine is a protected glycine derivative bearing an N-(9H-fluorenylmethoxycarbonyl) (Fmoc) group and a side chain substituted at the 2-position with a 6'-octenyl (alkenyl) functionality. The molecule contains a free carboxyl group and an Fmoc-protected amino group, with the (S) stereochemical designation applying to the α-carbon of the glycine scaffold. It is used as a building block for peptide synthesis, including solid-phase peptide synthesis workflows, where the Fmoc protection supports stepwise chain assembly and the pendant alkenyl handle can serve as a functional group for subsequent chemical modification or conjugation.
CAT No: HB00059
CAS No:1058705-57-9
Synonyms/Alias:(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)non-8-enoic acid
Chemical Name:(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)non-8-enoic acid
(S)-N-Fmoc-2-(6'-octenyl)glycine is an Fmoc-protected glycine derivative bearing a (6'-octenyl) side chain, providing a hydrophobic, alkene-containing functionality for downstream chemical modification. The (S)-stereochemistry at the alpha-carbon makes it a stereodefined amino acid building block for peptide synthesis workflows where the side chain geometry and reactivity are important. In practice, the allylic alkene enables post-coupling functionalization strategies while the Fmoc group supports standard orthogonal protection handling during assembly of modified peptides and peptide-based materials.
1. Peptide Synthesis Building Block
(S)-N-Fmoc-2-(6'-octenyl)glycine is used as a side-chain functionalized amino acid building block in custom peptide synthesis, particularly when researchers need an alkene handle embedded at a defined position within a peptide sequence. Solid-phase peptide synthesis workflows commonly incorporate this Fmoc amino acid to generate peptides that retain a pendant unsaturation for later derivatization, enabling structure-function studies and modular peptide construction. Peptide chemists and platform groups use it to prepare analog libraries where the hydrophobic octenyl side chain and the stereodefined backbone contribute to consistent physicochemical properties across variants.
2. Alkene-Handle Bioconjugation
(S)-N-Fmoc-2-(6'-octenyl)glycine is frequently selected when a peptide or short peptidic scaffold must carry a chemically addressable alkene for subsequent conjugation chemistry. After peptide assembly, the (6'-octenyl) functionality provides a convenient reactive motif for attaching labels, linkers, or affinity tags in workflows that rely on alkene-based derivatization. Chemical biology groups use this approach to generate site-defined conjugates for binding studies, receptor/ligand interaction assays, and assay development where the conjugation site is controlled by the position of the amino acid within the peptide.
3. Functionalized Peptide Probes
(S)-N-Fmoc-2-(6'-octenyl)glycine supports the preparation of peptide probes that require a hydrophobic tether and a downstream attachment point for reporters or capture groups. Researchers in chemical biology and materials-oriented peptide research use the octenyl side chain as a handle to introduce additional functionality after synthesis, allowing rapid iteration of probe formats without redesigning the peptide backbone each time. This makes it practical for developing peptide-based reagents used in imaging-adjacent labeling workflows, affinity reagent generation, and mechanistic studies that benefit from modular attachment of detection or immobilization components.
4. Biomaterials Surface Functionalization
(S)-N-Fmoc-2-(6'-octenyl)glycine is used to create peptide-derived motifs that can be further functionalized and then incorporated into biomaterial surfaces or coatings. By embedding the (6'-octenyl) group into peptide segments, materials researchers can generate peptide linkers that later undergo derivatization to introduce adhesion, crosslinking, or immobilization features tailored to specific substrates. Biomaterials groups and interface scientists value this approach for building peptide-functionalized polymers, hydrogel components, and surface-presented ligands where a defined hydrophobic/alkene-bearing segment improves patterning and downstream coupling control.
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