Kazuhiro Kamiya

A new broad-spectrum aminoglycoside antibiotic complex, sporaricin. VI. Sporaricins C and D.

Two new aminoglycoside antibiotics, sporaricins C and D have been isolated from the culture broth of Saccharopolyspora hirsuta subsp. kobensis, which produced sporaricins A and B. The structures of sporaricins C and D have been determined to be 4-N-carbamoyl-glycylsporaricin B and 4-N-formylglycylsporaricin B, respectively. Sporaricins C and D are active against Gram-negative and Gram-negative bacteria including aminoglycoside-resistant strains.

Syntheses of 3-O-substituted 3-O-demethylsporaricins A

Abstract The 3- O -methyl group of sporaricin A has been replaced by other alkyl groups to give 3- O -(3-amino-2-hydroxypropyl)- ( 13 ), 3- O -(4-amino-2-hydroxybutyl)- ( 15 ), and 3- O -(2,3-dihydroxypropyl)-sporaricin A ( 14 ). The 3- O -methyl group of sporaricin B was selectively removed under acidic conditions, and an allyl group was introduced onto the 3-hydroxyl group. The 3- O -allyl compound was 4- N -glycylated, the allyl group epoxidized, and the product treated with sodium azide or potassium cyanide, or hydrolyzed. The respective derivative obtained was then reduced, or deprotected, or both, to give 13 , 15 , and 14 . These compounds showed high antibacterial activities against bacteria resistant to sporaricin A.