The Chemistry of Aminoglycoside Antibiotics from Pseudomonas fluorescence. II. Absolute Configuration of the Diaminopolyol, the Aglycone of P-2563 (P) (Sorbistin A₁) and P-2563 (A) (Sorbistin B)

Abstract

The plane structure of the aminopolyol moiety of the aminoglycoside antibiotics P-2563 (P) (1) and P-2563 (A) (2) was elucidated to be 1, 4-diamino-1, 4-dideoxyhexitol (3) from physico-chemical and spectroscopic characterizations. The absolute configuration of 3 was determined to be 2S, 3S, 4R and 5S on the basis of transformation of 3 into methyl 3, 6-diacetamido-2, 4-di-O-acetyl-3, 6-dideoxy-α-L-gulopyranoside (12) by the oxidation of the hydroxymethyl group at C-6.