9bic

N-Me-D-Leu2,D-Thr5-clovibactin

spinqualitylabelsall models 9bic, resolution 2.05Å Show:Asymmetric Unit Biological Assembly Drag the structure with the mouse to rotate   Export Animated Image   Print3D Structural highlights 9bic is a 8 chain structure with sequence from Eleftheria. Full crystallographic information is available from OCA. For a guided tour on the structure components use FirstGlance. Method: X-ray diffraction, Resolution 2.05Å Ligands: CD, DLY, DTH, MLU, SO4 Resources: FirstGlance, OCA, PDBe, RCSB, PDBsum, ProSAT Publication Abstract from PubMed Our laboratory reported the chemical synthesis and stereochemical assignment of the recently discovered peptide antibiotic clovibactin. The current paper reports an improved, gram-scale synthesis of the amino acid building block Fmoc-(2R,3R)-3-hydroxyasparagine-OH that enables structure-activity relationship studies of clovibactin. An alanine scan reveals that residues Phe(1), d-Leu(2), Ser(4), Leu(7), and Leu(8) are important for antibiotic activity. The side-chain amide group of the rare d-Hyn(5) residue is not essential to activity and can be replaced with a methyl group with a moderate loss of activity. An acyclic clovibactin analogue reveals that the macrolactone ring is essential to antibiotic activity. The enantiomer of clovibactin is active, albeit somewhat less so than clovibactin. A conformationally constrained clovibactin analogue retains moderate antibiotic activity, while a backbone N-methylated analogue is almost completely inactive. X-ray crystallography of these two analogues reveals that the macrolactone ring adopts a crown-like conformation that binds anions. Structure-Activity Relationship Studies of the Peptide Antibiotic Clovibactin.,Brunicardi JEH, Griffin JH, Ferracane MJ, Kreutzer AG, Small J, Mendoza AT, Ziller JW, Nowick JS J Org Chem. 2024 Sep 6;89(17):12479-12484. doi: 10.1021/acs.joc.4c01414. Epub , 2024 Aug 23. PMID:39178334 From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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