8ad7

Flavin-dependent tryptophan 6-halogenase Thal in complex with D-Trp

spinqualitylabelsall models 8ad7, resolution 2.33Å Show:Asymmetric Unit Biological Assembly Drag the structure with the mouse to rotate   Export Animated Image   Print3D Structural highlights 8ad7 is a 2 chain structure with sequence from Streptomyces albogriseolus. Full crystallographic information is available from OCA. For a guided tour on the structure components use FirstGlance. Method: X-ray diffraction, Resolution 2.33Å Ligands: DTR, GOL, PO4 Resources: FirstGlance, OCA, PDBe, RCSB, PDBsum, ProSAT Function A1E280_STRAO Publication Abstract from PubMed The late-stage site-selective derivatisation of peptides has many potential applications in structure-activity relationship studies and postsynthetic modification or conjugation of bioactive compounds. The development of orthogonal methods for C-H functionalisation is crucial for such peptide derivatisation. Among them biocatalytic methods are increasingly attracting attention. Tryptophan halogenases emerged as valuable catalysts to functionalise tryptophan (Trp), while direct enzyme-catalysed halogenation of synthetic peptides is yet unprecedented. Here, it is reported that the Trp 6-halogenase Thal accepts a wide range of amides and peptides containing a Trp moiety. Increasing the sequence length and reaction optimisation made bromination of pentapeptides feasible with good turnovers and a broad sequence scope, while regioselectivity turned out to be sequence dependent. Comparison of X-ray single crystal structures of Thal in complex with d-Trp and a dipeptide revealed a significantly altered binding mode for the peptide. The viability of this bioorthogonal approach was exemplified by halogenation of a cyclic RGD peptide. Enzymatic Late-Stage Halogenation of Peptides.,Schnepel C, Moritzer AC, Gafe S, Montua N, Minges H, Niess A, Niemann HH, Sewald N Chembiochem. 2022 Oct 19. doi: 10.1002/cbic.202200569. PMID:36259362 From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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