Fmoc-L-Val-CHN2 is an Fmoc-protected derivative of the amino acid valine bearing a terminal diazirine (CHN2) functionality on the side chain, placing it in the class of photo-crosslinking amino acid building blocks for peptide and bioconjugate synthesis. The molecule contains an Fmoc carbamate protecting group on the amino functionality and retains a free carboxyl group, while the valine backbone is specified as the L stereochemical form and the diazirine moiety provides a photo-reactive handle for covalent capture. In synthesis, it is employed as a protected amino acid component in stepwise assembly workflows such as solid-phase or solution-phase peptide synthesis to introduce a photo-crosslinkable residue for labeling, structure-function studies, and crosslinking-based mapping experiments.
CAT No: CP25516
CAS No:193148-58-2
Synonyms/Alias:AmbotzFAA1601;Fmoc-L-Val-CHN2;MolPort-008-267-697;193148-58-2
Chemical Name:N-alpha-(9-fluorenylmethyloxycarbonyl)-L-valinyl-diazomethane, (3S)-3-Fmoc-amino-1-diazo-4-methyl-2-pentanone
Fmoc-L-Val-CHN2 is an Fmoc-protected L-valine hydrazide-derived diazomethyl ketone equivalent bearing a CHN2 functionality that can participate in electrophilic and nucleophilic transformations under peptide-chemistry compatible conditions. The molecule contains the chiral valine α-center (L-configuration), a side-chain isopropyl group that preserves the steric and hydrophobic character of valine, and an Fmoc carbamate that supports orthogonal protection during solid-phase peptide synthesis. The diazo-related CHN2 motif introduces a reactive handle for downstream conversion into carbonyl-containing or heterocycle-forming motifs, enabling targeted functionalization beyond standard amino acid coupling. The combination of an Fmoc-protected amino terminus and a side-chain-compatible stereochemical framework makes Fmoc-L-Val-CHN2 suitable as a chiral, derivatizable amino acid building block and as a synthetic intermediate for constructing more complex peptide and peptidomimetic structures.
1. Peptide Synthesis
Fmoc-L-Val-CHN2 is employed in peptide building block workflows where an Fmoc-protected amino terminus enables stepwise peptide coupling and controlled N-deprotection on solid supports. The L-valine backbone provides the canonical α-amino acid geometry and an isopropyl side chain that maintains valine-like steric behavior in growing sequences. The CHN2 functionality can be carried through peptide assembly and then converted post-coupling to introduce carbonyl or reactive intermediates for further derivatization of the peptide scaffold. The resulting peptide derivatives can be used to probe sequence-dependent reactivity, generate functional peptide conjugates, or access peptidomimetic analogs derived from valine-containing segments.
2. Peptidomimetics Chemistry
Fmoc-L-Val-CHN2 is applied in peptidomimetic construction where the Fmoc-protected valine unit serves as a stereochemically defined scaffold for assembling analogs with modified functional groups at the amino acid level. The CHN2 handle enables downstream transformations that can generate new linkage types or introduce carbonyl-bearing motifs, supporting structure-guided design of peptide-like molecules. The maintained L-configuration and valine side-chain identity help preserve conformational and hydrophobic features relevant to molecular recognition studies. The compound can therefore be used to prepare functionalized peptidomimetic libraries and to generate analog series for comparative chemical biology and SAR investigations.
3. Side-Chain Functionalization
Fmoc-L-Val-CHN2 is utilized for amino acid derivatization strategies that introduce a diazo-derived CHN2 reactive site while retaining an Fmoc-protected N-terminus for orthogonal handling. The isopropyl valine side chain provides a hydrophobic anchor that can influence solubility and reactivity patterns of the resulting derivatives. The CHN2 functionality can be converted to carbonyl-containing or heteroatom-containing products, enabling targeted installation of functional groups onto valine-based intermediates used in downstream synthesis. The resulting functionalized amino acid derivatives can be incorporated into larger synthetic sequences, including peptide analogs, small-molecule fragments, and conjugation-ready intermediates.
4. Chemical Biology Probes
Fmoc-L-Val-CHN2 is suitable for chemical biology research requiring amino acid-based reactive handles that can be incorporated into peptides or peptide-like constructs for subsequent labeling steps. The Fmoc protection supports compatibility with peptide synthesis conditions, while the chiral L-valine framework provides stereochemical control that can affect binding or localization of the probe scaffold. The CHN2 motif acts as a controllable functional group for conversion into reactive intermediates that enable attachment of tags or formation of labeled derivatives under defined derivatization workflows. The compound can thus serve as a starting point for probe generation, including reactive peptide conjugates used to interrogate biomolecular interactions and biomolecule microenvironments.
5. Process Chemistry Intermediate
Fmoc-L-Val-CHN2 is relevant to process chemistry and fine chemical synthesis as a chiral, protected amino acid intermediate that integrates an Fmoc-protected amine with a transformation-ready CHN2 functionality. The orthogonal protection strategy provided by the Fmoc carbamate supports controlled deprotection and minimizes interference during multi-step manufacturing routes. The valine-derived stereocenter offers a defined chiral input that can reduce downstream stereochemical correction steps in derivative synthesis. The compound can be employed to manufacture functionalized amino acid derivatives and peptide-building blocks on scalable synthetic platforms where intermediate handling, protection/deprotection logic, and downstream conversion of the CHN2 functionality are central to route design.
6. Analytical Standards Development
Fmoc-L-Val-CHN2 is used in analytical research contexts where an Fmoc-protected L-valine derivative with a distinct CHN2 motif provides a chemically traceable reference material for method development. The combination of an Fmoc chromophore and a diazo-related functional group supports detection by LC-MS and related analytical platforms after conversion or derivatization to characteristic fragments. The defined L-configuration and valine side-chain structure help ensure that analytical signals correspond specifically to valine-based stereochemical inputs rather than generic amino acid mixtures. The compound can therefore support calibration, impurity tracking, and structural verification for peptide coupling chemistry, amino acid derivatization workflows, and peptidomimetic intermediate characterization.
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