This paper describes the step-wise Fmoc solid phase synthesis of a 95-residue peptide related to FAS death domain. Attempts to prepare this peptide employing conventional amino acid building blocks failed. However, by the judicious use of dimethyloxazolidine dipeptides of serine and threonine, the peptide could be readily prepared in remarkable purity by applying single 1 h coupling reactions.
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http://dx.doi.org/10.1002/psc.484 | DOI Listing |
Org Lett
January 2025
Department of Chemistry, University of Waterloo, 200 University Ave. West, Waterloo, Ontario, Canada N2L3G1.
The first total synthesis of cyclic depsipeptide antibiotic LL-A0341β (LL) is described. The configuration of the β-methyltryptophan (β-MeTrp) residue was established by preparing all four stereoisomers of Fmoc-β-MeTrp which were used for the synthesis of LL via Fmoc solid phase peptide synthesis. The most active of the four peptides was the one containing (2,3)-β-MeTrp.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of BioMolecular Sciences, University of Mississippi, Oxford, Mississippi 38655, United States.
-GalNAc glycans on glycoproteins with eight different core structures sharing a common α-glycosidic linkage (-GalNAc-α-Ser/Thr) are critical in various physiological and pathological processes. Among the eight -GalNAc glycan cores, core 2 characterized by a GlcNAcβ1-6(Galβ1-3)GalNAc structural motif plays a significant role in regulating diverse biological processes, such as immune response modulation, adhesive properties of selectins, and gastrointestinal tract protection. However, the large-quantity synthesis of core 2 containing glyco-amino acids for downstream solid-phase peptide synthesis is challenging.
View Article and Find Full Text PDFCurr Res Food Sci
November 2024
Department of Animal Science, Chungbuk National University, Cheongju, 28644, Republic of Korea.
Unlabelled: Due to the structural diversity and complex mechanisms of action of bioactive peptides, screening for specific functional peptides is often challenging. To efficiently screen bioactive peptides with antioxidant and anti-inflammatory effects from bovine hemoglobin, we employed bioinformatics methods to perform virtual enzymatic hydrolysis using online tools and predicted the bioactivity, toxicity, and sensitization scores of the resulting peptides. Molecular docking and molecular dynamics simulations with Keap1 and TLR4 were subsequently conducted to screen for antioxidant and anti-inflammatory peptides.
View Article and Find Full Text PDFJ Vis Exp
November 2024
Department of Chemistry & Biochemistry, Fairfield University.
A home-built apparatus to perform solid phase peptide synthesis (SPPS), assisted by microwave irradiation and heating, is presented. In contrast to conventional SPPS reaction vessels, which drain solvent and byproducts via a frit located at the bottom of the vessel, the presented apparatus employs a gas dispersion tube under vacuum to remove solvent, byproducts, and excess reagents. The same gas dispersion tube supplies nitrogen gas agitation of the SPPS beads during the reaction steps of coupling and deprotection.
View Article and Find Full Text PDFJDS Commun
November 2024
Department of Animal and Dairy Sciences, University of Wisconsin-Madison, Madison, WI 53706.
The pool of free, genetically encoded AA in plasma plays an essential role not only as substrate for every protein synthesized in the body but also as signaling molecules that regulate a wide range of physiological processes. Here we present a method for the analysis of 19 of the 20 encoded AA (except Cys) in dairy cow plasma. Isolated plasma or standards for the 19 AA were gravimetrically mixed with an internal standard mix consisting of C isotopes of each AA.
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