Novel antibiotics, amythiamicins. III. Structure elucidations of amythiamicins A, B and C.
The structures of novel antimicrobial antibiotics, amythiamicins A, B and C, were elucidated by chemical degradations and NMR spectral analyses. The main frame from C-1 to C-41 of these antibiotics was the same as that of amythiamicin D. Amino acid autoanalyses of amythiamicins A, B and C showed that these have another one mole of serine and proline in comparison with amythiamicin D. Stereochemistries of both amino acids were determined to be L by chiral HPLC. These seryl-prolyl residues in amythiamicins A, B and C are attached at C-41 through an oxazoline ring, amide and ester bond, respectively.
Institute of Microbial Chemistry, Tokyo, Japan.
K
K
Shimanaka
Y
Y
Takahashi
H
H
Iinuma
H
H
Naganawa
T
T
Takeuchi
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D047028:Macrocyclic Compounds; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011392:Proline / Q000032:analysis; D012694:Serine / Q000032:analysis; D013844:Thiazoles
D000900:Anti-Bacterial Agents; D047028:Macrocyclic Compounds; D013844:Thiazoles; C088498:amythiamicin A; C088500:amythiamicin C; C088499:amythiamicin B; D012694:Serine; D011392:Proline