Some novel semisynthetic actins
Some novel semisynthetic actins
Ketononactic acid and ketohomononactic acid were isolated from a Streptomyces griseus fermentation culture and shown to be present mainly as the (-) and (+) enantiomers respectively. Ketononactic acid was shown to be a biosynthetic precursor of nonactin. An unsuccessful attempt was made to prepare t-butyl 2-(2-hydr-oxy-ethyl)(2-tetra-hydrofur-5-yl)propanoate by the catalytic hydro-genation of 2-(2-hydro-xyethyl)-5-(1-t-butyl-oxycarbonyl)ethyl-idene-tetra-hydro-furan, which was prepared from 6-(phenyl-methoxy)-hexan-4-olide by reaction with t-butyl lithio-propion-ate followed by Raney nickel catalysed hydrogenolysis. Methyl 8-ketopropylnonactate was prepared by the sequential reaction of methyl ketononactate with trimethylsilyl trifluoromethanesulphonate, chloroethyl phenyl sulphide, and Raney nickel. Methyl 8-ketopropylnonactate was incorporated into novel actins in 61% specific and 35% absolute incorporation by S. griseus in the presence of cerulenin. Mass spectral analysis of the resulting material revealed the presence of a range of novel actins containing one or two propylnonactate residues. (D71563/87)
University of Southampton
Rickard, Timothy Mark Adrian
1986
Rickard, Timothy Mark Adrian
Rickard, Timothy Mark Adrian
(1986)
Some novel semisynthetic actins.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
Ketononactic acid and ketohomononactic acid were isolated from a Streptomyces griseus fermentation culture and shown to be present mainly as the (-) and (+) enantiomers respectively. Ketononactic acid was shown to be a biosynthetic precursor of nonactin. An unsuccessful attempt was made to prepare t-butyl 2-(2-hydr-oxy-ethyl)(2-tetra-hydrofur-5-yl)propanoate by the catalytic hydro-genation of 2-(2-hydro-xyethyl)-5-(1-t-butyl-oxycarbonyl)ethyl-idene-tetra-hydro-furan, which was prepared from 6-(phenyl-methoxy)-hexan-4-olide by reaction with t-butyl lithio-propion-ate followed by Raney nickel catalysed hydrogenolysis. Methyl 8-ketopropylnonactate was prepared by the sequential reaction of methyl ketononactate with trimethylsilyl trifluoromethanesulphonate, chloroethyl phenyl sulphide, and Raney nickel. Methyl 8-ketopropylnonactate was incorporated into novel actins in 61% specific and 35% absolute incorporation by S. griseus in the presence of cerulenin. Mass spectral analysis of the resulting material revealed the presence of a range of novel actins containing one or two propylnonactate residues. (D71563/87)
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Published date: 1986
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Local EPrints ID: 460717
URI: http://eprints.soton.ac.uk/id/eprint/460717
PURE UUID: 5cbed18e-e981-40c0-9b20-481e9acd9d92
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Date deposited: 04 Jul 2022 18:28
Last modified: 04 Jul 2022 18:28
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Author:
Timothy Mark Adrian Rickard
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