598
Ledvina, Jezek, Saman, Hribalova:
lysis: glutamic acid 1.05, 2-aminobutanoic acid 1.03, normuramic acid 0.94. For C19H32N4O11 2 H2O
(528.5) calculated: 43.17% C, 6.86% H, 10.60% N; found: 43.21% C, 6.75%H, 10.74% N.
6-O-Octadecanoyl-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine (8)
Compound 5 (380 mg, 0.4 mmol) in acetic acid (50 ml) was hydrogenolyzed in the presence of 10%
Pd/C catalyst (400 mg) at room temperature for 16 h and worked up analogously to compound 7.
The lyophilized product was chromatographed on a silica gel C18 column in methanol–water (9 : 1).
The homogeneous fractions were concentrated in vacuo and the residue was lyophilized from acetic
1
acid to give 200 mg (66%) of compound 8, [α]D +17° (c 0.1, acetic acid). For H and 13C NMR data
see Tables I and II. For C37H66N4O12 calculated: relative molecular mass 759.0, monoisotopic mass
758.5. FAB MS, m/z: 759.4 [M + H]+, 781.4 [M + Na]+. For C37H66N4O12 (759.0) calculated:
58.55% C, 8.76% H, 7.38% N; found: 58.67% C, 8.61% H, 7.20% N.
[6-O-(2-Tetradecylhexadecanoyl)-N-acetylnormuramoyl]-L-2-aminobutanoyl-D-isoglutamine (9)
Compound 6 (1.2 g, 1.084 mmol) in acetic acid (50 ml) was hydrogenolyzed in the presence of 10%
Pd/C catalyst (400 mg) at room temperature for 16 h and worked up analogously to compound 7.
The lyophilized product was chromatographed on a silica gel C18 column in methanol–water (9 : 1).
Homogeneous fractions were concentrated in vacuo and the residue was lyophilized from acetic acid
1
to yield 698 mg (69%) of compound 9, [α]D +13° (c 1.0, acetic acid). For H and 13C NMR data, see
Tables I and II. For C49H90N4O12 calculated: relative molecular mass 927.3, monoisotopic mass
926.7. FABMS, m/z: 927.9 [M + H]+, 949.9 [M + Na]+. For C49H90N4O12 (927.3) calculated:
63.46% C, 9.78% H, 6.04% N; found: 63.68% C, 9.96% H, 5.81% N.
The authors would like to express their thanks to Dr V. Pechanec for elemental analyses, Dr K. Ubik
for FAB MS spectra and to Mr J. Zbrozek for amino acid analyses. Part of this work was supported by
grant No. 203/96/0309 of the Grant Agency of the Czech Republic.
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Collect. Czech. Chem. Commun. (Vol. 63) (1998)