Glysperin, a new antibiotic complex of bacterial origin. II. Structures of glysperins A, B and C

Structures of glysperins A, B and C were determined on the basis of chemical degradation studies in conjunction with spectroscopic analyses. Glysperin A consisted of L-alanine, p-hydroxybenzoic acid, a C11-alkyl tetramine and four sugar moieties, three of which were identified as D-ribose, D-galactose and 2,4-diamino-2,4,6-trideoxy-D-galactose. The fourth sugar was a novel exoenose, 6-deoxy-D-xylo-hex-5-enose. Structural difference between glysperins A and B resided solely in the terminal polyamine moiety which was spermidine in glysperin B. Glysperin C contained D-glucose in place of the exoenohexose moiety of glysperin A. Glysperins A, B and C are, in some respects, structurally related to the glycocinnamoylspermidine Antibiotics, LL-BM 123 beta, gamma 1 and gamma 2.