Structure, Total Synthesis, and Biosynthesis of Chloromyxamides: Myxobacterial Tetrapeptides Featuring an Uncommon 6-Chloromethyl-5-methoxypipecolic Acid Building Block
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Structure, Total Synthesis, and Biosynthesis of Chloromyxamides : Myxobacterial Tetrapeptides Featuring an Uncommon 6-Chloromethyl-5-methoxypipecolic Acid Building Block. / Gorges, Jan; Panter, Fabian; Kjaerulff, Louise; Hoffmann, Thomas; Kazmaier, Uli; Müller, Rolf.
In: Angewandte Chemie - International Edition, 10.2018, p. 14270-14275.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Structure, Total Synthesis, and Biosynthesis of Chloromyxamides
T2 - Myxobacterial Tetrapeptides Featuring an Uncommon 6-Chloromethyl-5-methoxypipecolic Acid Building Block
AU - Gorges, Jan
AU - Panter, Fabian
AU - Kjaerulff, Louise
AU - Hoffmann, Thomas
AU - Kazmaier, Uli
AU - Müller, Rolf
PY - 2018/10
Y1 - 2018/10
N2 - Soil-living microbes are an important resource for the discovery of new natural products featuring great structural diversity that are reflective of the underlying biosynthetic pathways as well as incorporating a wide range of intriguing small-molecule building blocks. We report here the full structural elucidation, total synthesis, and biosynthesis of chloromyxamides, a new class of tetrapeptides that display an unprecedented 6-chloromethyl-5-methoxypipecolic acid (CMPA) substructure. Chemical synthesis—including an approach to access the CMPA unit—was pursued to confirm the structure of the chloromyxamides and enabled determination of the absolute configuration in the CMPA ring. A model for the nonribosomal assembly of chloromyxamides was devised on the basis of the combined evaluation of the biosynthetic gene cluster sequence and the feeding of stable isotope-labeled precursors. This provided insight into the formation of the various chloromyxamide derivatives and the biogenesis of the CMPA unit.
AB - Soil-living microbes are an important resource for the discovery of new natural products featuring great structural diversity that are reflective of the underlying biosynthetic pathways as well as incorporating a wide range of intriguing small-molecule building blocks. We report here the full structural elucidation, total synthesis, and biosynthesis of chloromyxamides, a new class of tetrapeptides that display an unprecedented 6-chloromethyl-5-methoxypipecolic acid (CMPA) substructure. Chemical synthesis—including an approach to access the CMPA unit—was pursued to confirm the structure of the chloromyxamides and enabled determination of the absolute configuration in the CMPA ring. A model for the nonribosomal assembly of chloromyxamides was devised on the basis of the combined evaluation of the biosynthetic gene cluster sequence and the feeding of stable isotope-labeled precursors. This provided insight into the formation of the various chloromyxamide derivatives and the biogenesis of the CMPA unit.
KW - biosynthesis
KW - myxobacteria
KW - natural products
KW - secondary metabolites
KW - total synthesis
U2 - 10.1002/anie.201808028
DO - 10.1002/anie.201808028
M3 - Journal article
C2 - 30088846
AN - SCOPUS:85054160613
SP - 14270
EP - 14275
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
ER -
ID: 203876274