Publications [#233448] of Andrew T. McPhail

Journal Articles

  1. Mallams, AK; Puar, MS; Rossman, RR; McPhail, AT; Macfarlane, RD; Stephens, RL, "Kijanimicin. Part 3. Structure and absolute stereochemistry of kijanimicin", Journal of the Chemical Society Perkin Transactions 1January,, 1983(7), 1497-1534, Royal Society of Chemistry (RSC) [Gateway.cgi], [doi].
    (last updated on 2026/01/21)

    Abstract:
    Kijanimicin, a novel antibiotic from Actinomadura kijaniata nov. sp. SCC1256 (ATCC 31588), has been shown by chemical degradation, spectroscopic studies, and X-ray crystallographic studies to have a unique tetrpnic acid structure. The molecule contains a branched chain tetrasaccharide moiety consisting of three units of 2,6-dideoxy-α-L-ribo-hexopyranose and one unit of 2,6-dideoxy-4-O-methyl-β-L-ribo-hexopyranose. The molecule also contains a novel nitrosugar, namely 2,3,4,6-tetradeoxy-4-methoxy-carbonylamino- 3-C-methyl-3-nitro-β-D-xylo-hexopyranose (D-kijanose), which is the third nitrosugar to be isolated from an antibiotic. The structure of L-rubranitrose is revised to D-rubranitrose. Evidence for the total structure, the absolute stereochemistry, and the solution conformation of kijanimicin is presented.