Synthesis of the bicyclo[7.3.0]dodecatrienediyne core of the C-1027 chromophore.

[reaction: see text] C-1027, an extremely potent antitumor agent, is composed of chromophore 1 and an apoprotein. Here we report a general and efficient route to the exceedingly reactive bicyclo[7.3.0]dodecatrienediyne core of 1, utilizing selenoxide elimination and epoxide deoxygenation to build the cyclopentadiene and enediyne structures, respectively.

Binding of glycoglycerolipid derived from membranes of Acholeplasma laidlawii PG8 and synthetic analogues to lymphoid cells.

A component that binds to human lymphoid cells was isolated from the membranes of Acholeplasma laidlawii PG8. The component was extracted using the Bligh-Dyer method and purified using a silica-gel column and TLC. The active component was identified as 3-O:-[2'-O-(alpha-D-glucopyranosyl)- 6'-O-acyl-alpha-D-glucopyranosyl]-1,2-di-O- acyl-sn-glycerol (GAGDG) using (1)H- and (13)C-NMR and GC-MS. The compositions of the major saturated fatty acids were nC (14) (17.8%), isoC(14) (10.7%) and nC (16) (34.9%) as determined by GC-MS. The amounts of unsaturated species were less than 10% of those of the corresponding saturated acids. GAGDGs which have three tetradecanoyl groups were synthesized. These synthetic GAGDGs, as well as GAGDGs derived from A. laidlawii membranes, had a high binding affinity for MOLT-4 and HUT-78 (human T cell lines), Raji (a B cell line), HL-60 (a monoblastoid cell line) and primary cultured human T cells. The binding affinities of GAGDGs with an isoC(14) acyl group was higher than those with nC(14) and nC(16) acyl groups. The binding to lymphoid cells reveals a novel biological activity of GAGDGs.