Structural investigation of the antibiotic actinoidin: identification of the tris(amino acid)

✍ Scribed by Fernc Sztaricskai; Constance M. Harris; Thomas M. Harris

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 237 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86435-2

✦ Synopsis

The fugitive triamino tricarboxylic acid, the last remaining unknown constituent of the glycopeptide antibiotic actinoidin, has been identified as monodechlorovancomycinic acid by investigation of the products of base hydrolysis of the aglycone.

Actinoidin, a metabolite of Proactinomyces actinoides, is a member of the vancomycin group of antibiotics.

1 Two forms of this glycopeptide (A and B) have been identified, both of which contain D-glucose, D-mannose, two 3-amino-2,3,6-trideoxyhexoses (L-acosamine and L-actinosamine), L-phenylalanine, and the bis(ary1 amino acid) actinoidinic acid2 but differ in that A contains 4-hydroxyphenylglycine whereas B contains 3-chloro-4-hydroxyphenylglycine.

3 An additional constituent of A and B is the tris(amino acid) Y which has been detected in two peptides resulting from partial acid hydrolysis of the antibiotics.4 The free tris(amino acid) has not been detected in hydrolysates, presumably because of acid-catalyzed degradation. We wish to propose structure 1 for the Y constituent on the basis of degradative studies described below.

Methylation of actinoidin sulfate with excess CH2N2 in 50% aqueous methanol (20", 24 hr)