(S)-3-(Fmoc-methylamino)cyclopentane-1-carboxylic acid is a protected amino acid derivative featuring a cyclopentane ring bearing a carboxylic acid at the 1-position and a secondary amino substituent at the 3-position that is substituted with an Fmoc group via a methylamino linkage. The molecule contains both an amino functionality (as an Fmoc-protected amine) and a free carboxyl group, and the (S) stereochemistry at the cyclopentane carbon is specified in the name, which defines the chiral configuration of the amino acid scaffold. In peptide chemistry and solid-phase peptide synthesis workflows, this Fmoc-protected analogue functions as a building block that supports stepwise chain assembly while the Fmoc group helps control chemoselectivity by protecting the amine during coupling and subsequent deprotection steps.
CAT No: CP03801
CAS No:48621-07-1
Synonyms/Alias:(3s,4s)-4-amino-3-hydroxy-6-methylheptanoic acid(Statine);
(S)-3-(Fmoc-methylamino)cyclopentane-1-carboxylic acid is a chiral, Fmoc-protected amino acid building block featuring a cyclopentane core and a secondary methylamino side chain. The (S)-stereochemistry and conformationally constrained ring make it a useful non-proteinogenic residue for controlling backbone geometry in peptide synthesis. With an Fmoc group for standard base-mediated handling, this reagent is commonly selected when medicinal chemistry teams need a cyclopentane-containing amino acid to probe structure-property relationships in peptidomimetic and constrained peptide formats.
1. Solid-Phase Peptide Synthesis
(S)-3-(Fmoc-methylamino)cyclopentane-1-carboxylic acid is used as an Fmoc amino acid building block for solid-phase peptide synthesis workflows, where the cyclopentane scaffold helps introduce conformational restriction into custom peptides. Peptide synthesis groups in academic and industrial medicinal chemistry use this residue to generate constrained analogs for SAR studies, especially when a more rigid backbone than acyclic amino acids is desired. The secondary methylamino side chain provides an additional functional handle that can influence local polarity and intramolecular interactions during assembly and downstream derivatization of the peptide product.
2. Peptidomimetic Medicinal Chemistry
(S)-3-(Fmoc-methylamino)cyclopentane-1-carboxylic acid supports peptidomimetic development by enabling incorporation of a conformationally biased amino acid motif into lead optimization libraries. Medicinal chemistry teams use cyclopentane-containing residues to tune three-dimensional shape and side-chain presentation in peptide-like scaffolds, often as part of iterative design cycles where multiple constrained variants are synthesized and evaluated in biochemical or biophysical assays. The Fmoc-protected form streamlines integration into peptide-based constructs, while the methylamino side chain offers a practical site for further functional modification after peptide assembly.
3. Structure-Property SAR Libraries
(S)-3-(Fmoc-methylamino)cyclopentane-1-carboxylic acid is frequently selected for constructing structure-property relationship libraries that compare constrained versus less constrained amino acid substitutions within otherwise matched peptide backbones. Research groups focused on conformational control and residue-level optimization use this building block to systematically vary steric and stereoelectronic features while maintaining a consistent synthetic platform. The (S)-configuration and ring constraint help ensure reproducible stereochemical outcomes across library members, making it a convenient choice for generating series of analogs where side-chain environment and backbone geometry are key experimental variables.
4. Side-Chain Functionalization Handles
(S)-3-(Fmoc-methylamino)cyclopentane-1-carboxylic acid provides a secondary methylamino side chain that can be leveraged for post-synthetic modification strategies on peptide products. Chemical biology and materials-focused peptide developers use this residue to introduce amino-containing functionality within peptide frameworks that can be carried forward into derivatization steps such as salt formation, coupling to activated electrophiles, or incorporation into further chemical transformations compatible with peptide scaffolds. This makes the building block attractive when the primary goal is not only constrained peptide assembly, but also retaining a chemically addressable site for downstream functionalization of peptide conjugates.
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