Polyoxin A, B, C, D, E, F, G, H, I, J, K, L, M

Structure

Polyoxin
PolyoxinR1R2R3
A CH2OH NPEdia
B OH CH2OH NPEdia
C OH H CH2OH NPEdia
D OH Carboxy NPEdia
E OH Carboxy NPEdia
F Carboxy NPEdia
G OH NPEdia
H Me NPEdia
I H NPEdia
J OH Me NPEdia
K H NPEdia
L OH H NPEdia
M OH H NPEdia
Producing organism
Streptomyces cacaoi var. asoensis
Biological activity
fungal cell wall synthesis inhibition
Abstract
Polyoxin A-M were found to be a new class of peptide nucleosides. Hydrolytic degradation of polyoxins afforded three groups of unusual α-L-amino acids, i.e., 1-(5'-amino-5'-deoxy-β-D-allofuranuronosyl)-5-hydroxymethyluracil (polyoxin C) or its three nucleobase analogs, 5-O-carbamoyl-2-amino-2-deoxy-L-xylonic acid or its 3-deoxy analog, and 3-ethylidene-L-azetidine-2-carboxylic acid. These structures were established on chemical and spectoroscopic evidence. 5'-Aminofuranuronoside common to all polyoxins constitutes a nucleoside with α-amino acid nature. Sequence analysis showed polyoxins are di- or tripeptide of these moieties. The structures so elucidated embody all the interesting chemical features of polyoxins.
References
isolation and structural determination
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    J Am Chem Soc, 91(26): 7490-7505 (1969) PMID: 5358618
  • Shibuya K, Tanaka M, Nanbata T, Isono K, Suzuki S.: Transformation of Polyoxins D, E, and F with Sodium Bisulfite.
    Agric Biol Chem, 36(7): 1229-1236 (1972) [ doi: 10.1271/bbb1961.36.1229 ]
  • Isono K and Suzuki S.: The Polyoxins: Pyrimidine Nucleoside Peptide Antibiotics Inhibiting Fungal Cell Wall Biosynthesis.
    Heterocycles, 13(1): 333-351(1979) [ doi: 10.3987/S-1979-01-0333 ]
  • Hanessian S, Fu JM, Tu Y, Isono K.: Structural identity and stereochemical revision of polyoximic acid.
    Tetrahedron Lett, 34(26): 4153-4156 (1993) [ doi: 10.1016/S0040-4039(00)60515-4 ]
  • Additional information