N-(tert-Butoxycarbonyl)-3-cyclopentyl-L-alanine is a Boc-protected amino acid with a cyclopentyl side chain providing hydrophobic bulk. The residue aids design of conformationally restricted peptides and modulation of tertiary packing. Researchers use it to investigate steric effects on folding and binding. Its stability suits advanced synthetic applications.
CAT No: R2126
CAS No:143415-31-0
Synonyms/Alias:143415-31-0;(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopentylpropanoic acid;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-CYCLOPENTYL-PROPIONIC ACID;N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine;N-Boc-L-Cyclopentylalanine;(2S)-3-cyclopentyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid;DTXSID30654055;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclopentylpropanoic acid;Boc-L-Cyclopentylalanine;Boc-Ala(cPen)-OH;Boc-(S)-3-Cyclopentylalanine;Boc-(S)-2-amino-3-cyclopentylpropanoic acid;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-CYCLOPENTYLPROPANOIC ACID;MFCD03094885;SCHEMBL3814592;DTXCID00604805;GBTWGGHVJJRREA-JTQLQIEISA-N;(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopentylpropanoicacid;(S)-2-(tert-butoxycarbonylamino)-3-cyclopentylpropanoic acid;AKOS016012945;AS-50446;DS-019155;CS-0011029;P10251;(S)-2-tert-butoxycarbonylamino-3-cyclopentylpropionic acid;(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopentylpropanoic acid (Boc-L-Ala(cPent)-OH);
N-(tert-Butoxycarbonyl)-3-cyclopentyl-L-alanine is a synthetic amino acid derivative characterized by the presence of a tert-butoxycarbonyl (Boc) protecting group and a cyclopentyl substitution on the L-alanine backbone. As a non-canonical amino acid, it serves as a valuable building block in peptide chemistry, offering unique steric and hydrophobic properties for the design of novel peptide sequences. The Boc group confers stability during synthesis, enabling selective deprotection and facilitating incorporation into complex peptide structures. Its distinctive cyclopentyl side chain allows researchers to explore conformational effects and modulate biological activity in peptide-based investigations.
Peptide Synthesis: Utilization of N-(tert-Butoxycarbonyl)-3-cyclopentyl-L-alanine is central to the assembly of custom peptides via solid-phase peptide synthesis (SPPS) and solution-phase methods. The Boc protection of the amino group ensures compatibility with a wide range of coupling reagents and orthogonal deprotection strategies, allowing for precise sequential addition of amino acid residues. Its incorporation enables the generation of peptides with enhanced steric bulk and altered hydrophobicity, which can be critical for studying structure-activity relationships or optimizing peptide stability.
Protein Engineering: The cyclopentyl-substituted side chain of this derivative is particularly useful in protein engineering research, where the introduction of non-standard amino acids can probe the effects of side-chain modifications on protein folding, stability, and function. By replacing native residues with this analog, scientists can systematically investigate the impact of increased side-chain rigidity and hydrophobic character, providing insights into protein dynamics, folding pathways, and the design of novel protein architectures.
Conformational Analysis: Researchers employ N-(tert-Butoxycarbonyl)-3-cyclopentyl-L-alanine to modulate and study peptide backbone conformations. The bulky cyclopentyl group introduces conformational constraints, which can stabilize specific secondary structures such as helices or turns. This property is leveraged in the design of model peptides for nuclear magnetic resonance (NMR) spectroscopy, circular dichroism (CD), or X-ray crystallography studies aimed at elucidating the relationship between side-chain structure and overall peptide conformation.
Peptidomimetic Design: In the development of peptidomimetics, the structural features of this compound are exploited to enhance metabolic stability and bioavailability of peptide-based molecules. The cyclopentyl moiety provides resistance to enzymatic degradation, while the Boc group allows for controlled deprotection and further functionalization. Researchers design analogs containing this residue to mimic bioactive peptides, modulate receptor interactions, or create inhibitors with improved pharmacokinetic properties for biochemical assays.
Analytical Reference Standard: The well-defined chemical structure and unique side-chain characteristics of N-(tert-Butoxycarbonyl)-3-cyclopentyl-L-alanine make it a suitable reference compound in analytical method development. Laboratories utilize it as a standard for validating chromatographic separation techniques, mass spectrometry calibration, or quantification of related synthetic intermediates. Its presence in analytical workflows supports accurate monitoring of peptide synthesis progress and quality control in research-scale manufacturing environments.
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