Normal: Smartphone (Charm +30) - 100 Diamond / 2000 Medal Premium: Memo Notebook (Charm +50) - 200 Diamond / 10000 Medal → CG Normal: Point-and-Shoot Camera (Charm +10) - 50 Diamond / 1000 Medal Sugar amino acids (SAAs) were designed and synthesized as new non-peptide peptidomimetics utilizing carbohydrates as peptide building blocks.Premium: SLR Camera (Charm +30) - 100 Diamond / 2000 Medal → CG They represent sugar-like ring structures that carry an amino and a carboxylic functional group and have a specific conformational influence on the backbone of peptides due to their distinct substitution patterns in rigid pyranose sugar rings. Linear and cyclic peptides involving SAAs have been prepared in solution as well as by solid phase synthesis.įive different SAAs (SAA 1α, SAA 1β, SAA 2, SAA 3, and SAA 4) have been synthesized that show the ability to constrain linear backbone conformations or distinct turn structures. SAA 1α and SAA 2 were incorporated into two linear Leu-enkephalin analogs, replacing the natural Gly-Gly dipeptide. NMR studies provide evidence for the conformation-inducing effect of the carbohydrate moiety. SAA 2 and SAA 3 have been placed in cyclic hexapeptide analogs of somatostatin SAA 4 was incorporated in a model peptide. The conformation of the cyclic peptides cyclo(-SAA 2-Phe- d-Trp-Lys-Thr-), cyclo(-SAA 3-Phe- d-Trp-Lys(Boc)Thr(tBu)-), and cyclo(-SAA 4-Ala- d-Pro-Ala-Ala-) have been analyzed by various NMR techniques in combination with distance geometry calculations and subsequent molecular dynamic simulations. The determined solution conformations were compared to representative idealized peptide backbones. SAA 2 and SAA 3 induce a β-turn structure while SAA 4 mimics a γ-turn. Both enkephalin analogs were not active in the guinea pig ileum assay. The somatostatin analog containing SAA 2 has an inhibition constant (IC 50) of 0.15 μM for the inhibition of the release of growth hormone. Rasha Jwad, Daniel Weissberger, Luke Hunter.This article is cited by 160 publications. Strategies for Fine-Tuning the Conformations of Cyclic Peptides. Burade, Sopan Valiba Shinde, Naresh Bhuma, Navanath Kumbhar, Amol Kotmale, Pattuparambil R. The Journal of Organic Chemistry 2017, 82 Acyclic αγα-Tripeptides with Fluorinated- and Nonfluorinated-Furanoid Sugar Framework: Importance of Fluoro Substituent in Reverse-Turn Induced Self-Assembly and Transmembrane Ion-Transport Activity. Marlen Malke, Haitham Barqawi, and Wolfgang H.The Journal of Organic Chemistry 2015, 80 Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics. Synthesis of an Amphiphilic β-Turn Mimetic Polymer Conjugate. Journal of the American Chemical Society 2012, 134 Poly-amido-saccharides: Synthesis via Anionic Polymerization of a β-Lactam Sugar Monomer. Carine Bughin, Géraldine Masson, and, Jieping Zhu.The Journal of Organic Chemistry 2010, 75 SnCl4- and TiCl4-Catalyzed Anomerization of Acylated O- and S-Glycosides: Analysis of Factors That Lead to Higher α:β Anomer Ratios and Reaction Rates. The Journal of Organic Chemistry 2007, 72 Rapid Synthesis of Cyclodepsipeptides Containing a Sugar Amino Acid or a Sugar Amino Alcohol by a Sequence of a Multicomponent Reaction and Acid-Mediated Macrocyclization. Carsten Baldauf, Robert Günther, and, Hans-Jörg Hofmann.Synthesis of Somatostatin Mimetics Based on the 1-Deoxymannojirimycin Scaffold. Manuela Tosin, Colin O'Brien, Geraldine M.Control of Helix Formation in Vinylogous γ-Peptides by (E)- and (Z)-Double Bonds: A Way to Ion Channels and Monomolecular Nanotubes. The Journal of Organic Chemistry 2005, 70 Synthesis and Structural Analysis of the Anilides of Glucuronic Acid and Orientation of the Groups on the Carbohydrate Scaffolding.
0 Comments
Leave a Reply. |
AuthorWrite something about yourself. No need to be fancy, just an overview. ArchivesCategories |