N-Fmoc-6-Methoxy-D-Tryptophan offers a fluorescent, methoxy-substituted indole ring combined with D-chirality for stereochemical probing. The Fmoc protection allows direct incorporation into peptides during solid-phase synthesis. Researchers use it to tune photophysical properties and investigate chiral recognition. Applications include fluorescent probe design, conformational analysis, and tryptophan-analog screening.
CAT No: R2185
Synonyms/Alias:N-Fmoc-6-Methoxy-D-tryptophan;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(6-methoxy-1H-indol-3-yl)propanoic acid
N-Fmoc-6-Methoxy-D-tryptophan is a specialty amino acid derivative widely recognized for its unique structural characteristics and functional versatility in synthetic organic chemistry and peptide science. Featuring a 6-methoxy substitution on the indole ring and an N-terminal Fmoc protecting group, this compound is tailored for applications requiring high specificity and orthogonality during peptide synthesis. The D-configuration further distinguishes it from its L-counterpart, imparting distinct conformational and biological properties to the peptides or molecules into which it is incorporated. Researchers value N-Fmoc-6-Methoxy-D-tryptophan for its ability to introduce both steric and electronic modifications, enabling the exploration of novel structure-activity relationships in peptide-based studies and beyond.
Peptide Synthesis: N-Fmoc-6-Methoxy-D-tryptophan serves as a critical building block in solid-phase peptide synthesis (SPPS), particularly for the generation of peptides with enhanced stability or altered receptor interactions. The Fmoc group is compatible with widely used deprotection strategies, allowing sequential assembly of peptide chains without compromising the integrity of the methoxy-modified indole ring. Incorporation of this D-amino acid analog can confer resistance to enzymatic degradation and influence the overall conformation of the resulting peptide, making it valuable for the design of research peptides with extended half-lives or unique folding properties. Medicinal Chemistry: In the field of medicinal chemistry, the compound is utilized to modify the pharmacokinetic and pharmacodynamic profiles of peptide-based lead compounds. The 6-methoxy substituent modulates electronic distribution on the indole ring, potentially enhancing target binding affinity or selectivity. Additionally, the D-configuration can reduce off-target interactions and improve metabolic stability, supporting the development of peptide mimetics and small molecule libraries for exploratory research. Structure-Activity Relationship Studies: 6-Methoxy-D-tryptophan derivatives are instrumental in systematic structure-activity relationship (SAR) investigations, wherein subtle modifications are introduced to probe the roles of specific side chain functionalities. By incorporating this analog into model peptides or peptidomimetics, researchers can dissect the contributions of the indole ring's electronic and steric environment to biological activity, informing rational design strategies for future analogs. Fluorescence and Spectroscopic Probes: The presence of a methoxy group on the indole ring can alter the compound's photophysical properties, making it an attractive candidate for use as an intrinsic probe in fluorescence-based assays or spectroscopic analyses. Its unique emission profile enables the monitoring of peptide folding, binding events, or localization in complex biological environments, facilitating detailed mechanistic studies and real-time tracking of molecular interactions. Chemical Biology Tools: N-Fmoc-6-Methoxy-D-tryptophan is also employed as a chemical biology tool for the selective modification and labeling of peptides or proteins. Its orthogonal reactivity and distinct chemical signature allow for site-specific incorporation into larger biomolecules, supporting the development of conjugates for imaging, affinity capture, or functional modulation experiments.
Protein Engineering: The versatility of this tryptophan analog extends to protein engineering applications, where site-directed incorporation can elucidate the role of specific residues in protein folding, stability, or function. By substituting native tryptophan residues with the 6-methoxy-D isomer, scientists can probe the effects of altered side chain electronics and chirality on protein structure and activity, advancing our understanding of protein dynamics and informing the design of engineered proteins with tailored properties. N-Fmoc-6-Methoxy-D-tryptophan thus stands as a multifaceted reagent, empowering researchers across disciplines to interrogate and manipulate peptide and protein systems with precision and creativity.
3. Emu oil in combination with other active ingredients for treating skin imperfections
4. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment
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