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Search for "hydroxymalonyl-ACP" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

  • Enjuro Harunari,
  • Hisayuki Komaki and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

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  • valine and its C-methylation with methionine and the polyol carbons are derived from a glycolysis intermediate, possibly hydroxymalonyl-ACP. Keywords: biosynthesis; butyrolactol; contiguous polyol; hydroxymalonyl-ACP; polyketide; Streptomyces; tert-butyl; Introduction Actinomycetes produce structurally
  • to C-4) and the pentaol (C-5 to C-9) moieties (Figure 3), suggesting that the contiguous polyol system is not formed by methylene hydroxylation. Another possible pathway for 1,2-diol formation is the incorporation of hydroxymalonyl-ACP from a glycolytic intermediate for chain elongation [23]. To
  • investigate this possibility, we conducted a feeding experiment of [U-13C6]glucose which could label carbons derived from malonyl-CoA and hydroxymalonyl-ACP. In the 13C NMR spectrum, 13C–13C couplings were observed for C-1/C-2, C-3/C-4, C-5/C-6, C-7/C-8 in addition to the carbon pairs C-11/C-12, C-13/C-14, C
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Published 08 Mar 2017

Polyketide stereocontrol: a study in chemical biology

  • Kira J. Weissman

Beilstein J. Org. Chem. 2017, 13, 348–371, doi:10.3762/bjoc.13.39

Graphical Abstract
  • [39] are employed. However, more recent crystallographic work on the zwittermicin pathway [43] in which hydroxymalonyl-ACP is used as extender unit, has raised some uncertainty over the hydroxymalonyl stereochemistry, as the (2S)-isomer would appear to fit better within the investigated AT structure
  • stereochemistry can be introduced at several points within the pathways. For example, although fatty acids are constructed primarily from malonyl-CoA units, the AT domains of cis-AT PKSs exhibit specificity towards a number of branched extender units (including methylmalonyl-CoA, ethylmalonyl-CoA, hydroxymalonyl
  • -ACP, methoxymalonyl-ACP, etc. [15][16]), thus incorporating pendant functionality into the polyketide skeleton (C-2-methyl, C-2-ethyl, C-2-hydroxy and C-2-methoxy groups, respectively). In the case of erythromycin A (1) (Figure 2 and Figure 3), for example, the C-2-methyl groups resulting from use of
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Published 24 Feb 2017
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