This serine analog contains a cyclohexyl ether substituent that enhances steric mass and modulates polarity. The Fmoc protection facilitates controlled incorporation into peptide frameworks. Researchers employ it to examine hydrogen-bonding modulation and conformational restriction. Its hydrophobic substituent supports exploration of membrane-associated environments.
CAT No: R2181
CAS No:221057-20-1
Synonyms/Alias:N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine;221057-20-1;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-cyclohexyl-L-serine //;CS-0120121;G81888;EN300-6513030;(2S)-3-(cyclohexyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;
N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine is a specialized carbohydrate-derived amino acid derivative widely recognized for its utility in the field of peptide synthesis and chemical biology. Characterized by the presence of the fluorenylmethyloxycarbonyl (Fmoc) protecting group and a cyclohexyl modification on the serine side chain, this compound offers enhanced stability and unique reactivity profiles, making it a valuable intermediate for constructing complex biomolecular architectures. Its structural features allow for selective manipulation and integration into synthetic sequences, supporting the development of advanced research tools and facilitating the study of protein structure and function.
Peptide Synthesis: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine is extensively employed as a building block in solid-phase peptide synthesis (SPPS). The Fmoc group serves as a temporary protecting group for the amino terminus, allowing sequential elongation of peptide chains with high fidelity. The cyclohexyl modification on the serine hydroxyl side chain provides steric hindrance and modulates the reactivity, which can be exploited to prevent undesired side reactions and improve the overall yield and purity of synthesized peptides. Researchers often utilize this derivative to introduce O-cyclohexyl serine residues into peptides, enabling the generation of modified sequences with enhanced stability or altered biological properties, thus expanding the scope of peptide engineering.
Chemical Biology Probes: The unique structure of N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine allows it to serve as a precursor for the development of chemical probes used in the investigation of protein-ligand interactions. By incorporating this residue into peptides or small molecules, scientists can modulate hydrophobicity and steric environment, facilitating the design of probes with improved selectivity and binding affinity. Such probes are instrumental in elucidating the mechanisms of enzyme recognition, substrate specificity, and protein-protein interactions, thereby advancing our understanding of complex biological systems at the molecular level.
Proteomics Research: In proteomics, the incorporation of O-cyclohexyl-L-serine derivatives into synthetic peptides enables the generation of standards and calibration tools for mass spectrometry-based analyses. The distinctive mass and chemical properties of this modified amino acid facilitate the differentiation and quantification of peptides in complex mixtures. As a result, it supports the development of robust analytical workflows for protein identification, post-translational modification mapping, and quantitative proteomics, providing researchers with reliable reference materials for high-precision studies.
Drug Discovery and Design: The inclusion of N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine in peptide libraries accelerates the screening and optimization of bioactive compounds. Its cyclohexyl group imparts conformational rigidity and hydrophobicity, attributes that can enhance the binding affinity and metabolic stability of lead peptides or peptidomimetics. Medicinal chemists leverage these features to design molecules with improved pharmacological profiles, supporting the identification of novel ligands and therapeutic candidates for a range of biological targets.
Biomaterials Engineering: The unique chemical and structural characteristics of this serine derivative have also been harnessed in the creation of functionalized biomaterials. By integrating O-cyclohexyl-L-serine into peptide-based hydrogels, scaffolds, or surface coatings, material scientists can tailor the mechanical properties, biocompatibility, and surface interactions of these constructs. Such modifications enable the development of advanced materials for tissue engineering, biosensing, or controlled delivery applications, demonstrating the versatility and research value of N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclohexyl-L-serine in interdisciplinary scientific endeavors.
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