Gln(Acm)3-Desmopressin contains Acm-protected glutamine variants to stabilize side-chain reactivity during synthetic manipulation. The modified residues alter hydrogen bonding and local polarity. Researchers use it to study protection-group effects on folding and ring geometry. Applications include peptide-synthesis strategy development, structural comparison, and analog preparation.
CAT No: R2881
Synonyms/Alias:deamino-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl(Acm)-L-asparagyl-L-cysteinyl-L-prolyl-D-arginyl-glycinamide (1->6)-disulfide; deamino-Cys-Tyr-Phe-Gln(Acm)-Asn-Cys-Pro-D-Arg-Gly-NH2 (Disulfide bridge: Cys1-Cys6); Mpr-Tyr-Phe-Gln(Acm)-Asn-Cys-Pro-D-Arg-Gly-NH2 (Disulfide Bridge Mpr1-Cys6)
Gln(Acm)3-Desmopressin is a synthetic peptide analog derived from desmopressin, featuring three acetamidomethyl (Acm) protected glutamine residues. As a chemically modified peptide, it is designed for advanced research applications where site-specific protection and controlled peptide functionality are critical. The incorporation of Acm groups onto glutamine side chains enables selective deprotection strategies during peptide synthesis, making this compound particularly valuable for the development of complex peptide architectures and the study of structure-function relationships. Its unique design supports a range of investigations in peptide chemistry, molecular biology, and bioanalytical research, providing researchers with a versatile tool for probing peptide behavior and optimizing synthetic protocols.
Peptide Synthesis: Gln(Acm)3-Desmopressin serves as a specialized building block in solid-phase peptide synthesis (SPPS) and solution-phase peptide assembly. The Acm-protected glutamine residues allow for orthogonal protection, facilitating stepwise elongation and selective modification of the peptide chain. This protection strategy is particularly important in the synthesis of peptides containing multiple reactive side chains, where precise control over deprotection steps is necessary to avoid unwanted side reactions. Researchers utilize this compound to construct high-fidelity peptide analogs and to explore synthetic methodologies that require differentiated side-chain protection.
Structure-Function Studies: The availability of site-specifically protected glutamine residues in this peptide analog enables detailed investigations into the structural and functional consequences of side-chain modifications. By incorporating Gln(Acm)3-Desmopressin into experimental systems, scientists can study how the presence or removal of protective groups influences peptide folding, receptor binding, and biochemical activity. These insights are essential for elucidating the roles of specific amino acid residues in peptide-protein interactions and for designing analogs with tailored properties.
Disulfide Bond Engineering: The Acm protecting group is known for its stability under conditions that preserve disulfide linkages, making this compound especially useful in the synthesis of peptides with complex disulfide architectures. Researchers can selectively remove Acm groups after initial peptide assembly to introduce additional modifications or to generate peptides with multiple, precisely positioned disulfide bonds. This application is crucial in the production of bioactive peptides and mini-proteins that require defined three-dimensional conformations for biological or analytical studies.
Analytical Method Development: As a chemically defined, protected peptide, Gln(Acm)3-Desmopressin provides a reliable reference standard for developing and validating analytical techniques such as HPLC, mass spectrometry, and peptide mapping. Its unique structural features allow method developers to assess the specificity, sensitivity, and reproducibility of analytical workflows targeting protected or modified peptides. The compound's stability and defined composition make it a valuable control in quality assurance and method optimization protocols.
Peptide Modification Research: The presence of multiple Acm-protected glutamine residues offers a versatile platform for exploring new strategies in peptide modification and functionalization. Researchers can selectively deprotect and derivatize these sites to introduce novel chemical functionalities, fluorescent labels, or cross-linking moieties. Such modifications expand the utility of the peptide for applications in bioconjugation, molecular imaging, and the creation of multifunctional peptide probes for advanced biochemical investigations.
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