N-Fmoc-O-cyclopropyl-L-serine features a cyclopropyl ether substituent that introduces rigidity and steric enhancement. Researchers employ it to analyze constrained hydrogen bonding, backbone alignment, and helix modulation. Its unusual side chain aids in designing structured peptide frameworks. Fmoc protection ensures synthetic compatibility.
CAT No: R2119
CAS No:2642331-45-9
Synonyms/Alias:N-Fmoc-O-cyclopropyl-L-serine;SCHEMBL24633712;2642331-45-9;CS-0439404;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-cyclopropyl-L-serine;
N-Fmoc-O-cyclopropyl-L-serine is a synthetic amino acid derivative distinguished by the presence of both an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group and a cyclopropyl modification on the serine side chain. As a non-standard amino acid, it is engineered for advanced peptide synthesis and structure-activity relationship studies, offering unique steric and electronic properties compared to its natural counterpart. Its incorporation into peptide sequences enables researchers to probe the effects of constrained ring systems on peptide conformation, stability, and biological function, making it a valuable tool in contemporary peptide chemistry and biochemical research.
Peptide Synthesis: Utilization of N-Fmoc-O-cyclopropyl-L-serine in solid-phase peptide synthesis (SPPS) allows for the site-specific introduction of a cyclopropyl group onto the serine residue. The Fmoc protecting group facilitates stepwise chain elongation under mild conditions, preserving side-chain integrity. Incorporating this modified residue enables the generation of peptides with enhanced conformational rigidity or altered hydrophobicity, which can be critical for studying backbone dynamics, helix propensity, or the influence of side-chain constraints on peptide folding.
Peptidomimetic Design: The cyclopropyl ring in the serine side chain introduces conformational constraints that are often exploited in the design of peptidomimetics. Researchers employ this derivative to mimic β-turns, γ-turns, or other secondary structures, thereby modulating bioactive conformations and improving resistance to enzymatic degradation. Such modifications are instrumental in developing peptide analogs with optimized binding characteristics or improved metabolic stability for biochemical and pharmacological investigations.
Structure-Activity Relationship (SAR) Studies: Incorporation of N-Fmoc-O-cyclopropyl-L-serine into peptide libraries enables systematic evaluation of the impact of side-chain cyclopropylation on biological activity and molecular recognition. By substituting canonical serine with its cyclopropyl analog, researchers can dissect the steric and electronic contributions of the side chain to receptor interactions, enzyme substrate specificity, or protein-protein interactions, thereby deepening mechanistic insights into peptide function.
Chemical Biology Probes: The unique structural features of this Fmoc-protected amino acid derivative make it suitable for the development of chemical biology probes. When integrated into peptides or small molecules, the cyclopropyl group can serve as a conformational reporter or a steric block, providing a means to interrogate protein-ligand interactions, map binding sites, or modulate access to specific residues. Such probes are valuable in elucidating complex biochemical pathways and protein functions in vitro.
Analytical Method Development: Owing to its non-canonical structure and distinct physicochemical properties, N-Fmoc-O-cyclopropyl-L-serine is also used as a reference standard or calibration compound in analytical method development. Its unique mass and chromatographic behavior facilitate the validation of peptide purification protocols, mass spectrometric detection, and the assessment of synthetic efficiency during peptide assembly. Employing this derivative in analytical workflows supports rigorous quality control and method optimization in peptide chemistry laboratories.
1. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
3. Peptides as Active Ingredients: A Challenge for Cosmeceutical Industry
5. Emu oil in combination with other active ingredients for treating skin imperfections
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More