Fmoc-alpha-Octenyl-D-Ala-OH

Fmoc-alpha-Octenyl-D-Ala-OH is an Fmoc-protected, D-configured alanine derivative bearing a terminal alkenyl side chain (octenyl) that can participate in alkene-selective transformations and hydrophobic scaffold design. The molecule contains the Fmoc carbamate on the amino terminus and a free carboxylic acid at the C-terminus, enabling standard peptide coupling while preserving orthogonality between N-deprotection and side-chain chemistry. The D-stereocenter at the alanine backbone provides stereochemical control for incorporating D-amino acid motifs into peptides, affecting conformational preferences and protease resistance profiles in peptide analogs. The pendant terminal alkene introduces an additional functional handle for downstream derivatization without disturbing the protected amine chemistry during protected amino acid synthesis and peptide assembly.

1. Peptide Synthesis

Fmoc-alpha-Octenyl-D-Ala-OH supports solid-phase peptide synthesis and fragment coupling workflows where an Fmoc-protected D-amino acid building block is required. The Fmoc group enables on-resin N-deprotection strategies while the free carboxylic acid participates in amide bond formation to build peptide backbones under standard peptide coupling conditions. The D-configuration at the alpha-carbon allows stereodefined incorporation of D-Ala units, and the octenyl side chain can be carried through assembly as an alkene handle for post-coupling functionalization. Downstream peptide analogs prepared from this building block can be further modified to introduce hydrophobic patches, crosslinkable motifs, or alkenyl-reactive handles for structure-activity relationship studies and peptide chemistry investigations.

2. Peptidomimetics

Fmoc-alpha-Octenyl-D-Ala-OH is suitable for peptidomimetic construction where controlled stereochemistry and side-chain functionality are used to tune molecular recognition and conformational behavior. The combination of an Fmoc-protected N-terminus and a terminal alkene side chain enables sequential design steps: peptide or peptidomimetic assembly followed by selective alkene functionalization to generate new binding surfaces or constrained architectures. D-amino acid incorporation can be applied to modulate backbone geometry and reduce susceptibility to proteolysis in peptide analog libraries, supporting medicinal chemistry and molecular design programs. The resulting alkenyl-functional peptidomimetics can serve as intermediates for generating analog series through side-chain derivatization while maintaining a stereochemically defined core.

3. Side-Chain Functionalization

Fmoc-alpha-Octenyl-D-Ala-OH provides a terminal alkene functionality positioned on a D-Ala scaffold, enabling post-synthetic transformations that are compatible with amino acid derivative workflows. The protected amino group (Fmoc) and free carboxyl group allow the compound to be used as a stable intermediate during derivatization planning, with orthogonality between backbone coupling chemistry and side-chain reactivity. Terminal alkene reactivity can be leveraged to introduce additional functional groups, generate cyclization motifs, or install chemical handles for subsequent conjugation steps after peptide assembly. The product thereby functions as a chiral amino acid intermediate for producing derivatized amino acid derivatives and downstream conjugation-ready molecules in chemical biology and synthetic organic chemistry.

4. Bioconjugation Chemistry

Fmoc-alpha-Octenyl-D-Ala-OH can be applied to bioconjugation strategies where peptide-based linkers require both stereochemical definition and a reactive side-chain handle. The alkenyl side chain can be used as a chemical handle for coupling or attachment chemistries after peptide or linker construction, while the D-amino acid backbone supports defined spatial presentation of the linker in biomolecule-modified constructs. The Fmoc-protected amine supports preparation of peptide linkers under controlled N-terminal chemistry, and the carboxylic acid enables incorporation into amide-linked conjugate architectures. Downstream conjugates prepared from this amino acid derivative can be used in biochemical research workflows such as probe construction, affinity reagent generation, and structure-defined biomolecule labeling.

5. Process Chemistry Intermediate

Fmoc-alpha-Octenyl-D-Ala-OH is suitable as a chiral building block intermediate in process chemistry and fine chemical synthesis where robust protection/deprotection logic is required. The Fmoc carbamate provides a manufacturable N-protection strategy that can be removed on demand during peptide assembly, while the free carboxylic acid supports coupling chemistry without requiring late-stage functional group rearrangement. The D-stereocenter and terminal alkene side chain allow downstream conversion into functional derivatives while keeping the core stereochemical identity intact through intermediate handling. The compound can therefore be employed in scalable peptide-building block preparation and manufacturing route design for stereodefined amino acid derivatives used in peptide science, peptidomimetic pipelines, and applied chemical manufacturing.

1. Effect of Probiotic Lactobacillus plantarum on Streptococcus mutans and Candida albicans Clinical Isolates from Children with Early Childhood Caries

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

3. cRGD-functionalized, DOX-conjugated, and 64Cu-labeled superparamagnetic iron oxide nanoparticles for targeted anticancer drug delivery and PET/MR imaging

4. Proinsulin C-peptide and insulin: Limited pattern similarities of interest in inter-peptide interactions but no C-peptide effect on insulin and IGF-1 receptor signaling

5. Odorant binding protein based biomimetic sensors for detection of alcohols associated with Salmonella contamination in packaged beef