Cyclopeptid‐Antibiotika aus Aspergillus‐Arten. Struktur der Echinocandine C und D

Abstract

Cyclapeptide antibiotics from Aspergillus species. Structure of echinocandins C and D SummuryThe echinocandins B, C and D are antifungal antibiotics produced by a strain of Aspergillus rugulosus. All three metabolites are closely related representing cyclic oligopeptides composed of six amino acids and a linolic acid residue in an amide linkage. The complete structure of echinocandin B (1) has recently been established by X-ray analysis. Structural assignments to the new minor metabolites C and D have now been made by hydrolytic and oxidative cleavage reactions, formation of N-acyl-u-aminoethers as well as by chemical correlations and extensive NMR. examinations. Echinocandin C (2), CS2H8 15, contains 3-hydroxyhomotyrosine in the place of 3,4-dihydroxyhomotyrosiiie present in 1. Ikhinocandin D (3), C,,H,IN,O 13, differs in two amino acids: 3,4-dihydroxyhomotyrosine and 4,5-dihydroxyornithine, unusual units of 1 being replaced by 3-hydroxyhomotyrosine and ornithine.

Lipopeptides as anti-infectives: a practical perspective

“…While the echinocandin B (ECB) structure was determined by chemical degradation studies in combination with X-ray crystallographic analysis [87,88], the structures of echinocandins C and D were elucidated by their conversion into a common intermediate derived from the B form [89]. They are all acylated at the N-terminus with a linoleic acid molecule.…”

Discovery of Novel Antifungal (1,3)-β- d -Glucan Synthase Inhibitors

“…Approximately 0.3 to 1% of MK-0991 is orally absorbed in mice (1), while in dogs 9% of the LY303366 dose is orally bioavailable (60; L. Zornes Until now, only two chemical classes of compounds, the lipopeptides and papulacandins, have been known to inhibit (1,3)-␤-D-glucan synthase. In the 1970s, the echinocandins were the first members of the lipopeptide group to be discovered, and the entire class is often referred to by this term (40,55). The compounds are cyclic hexapeptides N-linked to a fatty acyl side chain.…”

Fungal Metabolites for the Control of Biofilm Infections

“…Later, a number of similar compounds were discovered and their biological activities were characterized [111]. These compounds include: echinocandins C 79 and D 80 from Aspergillus rugulosus [112]; aculeacin Aα 74, Aγ 75, Dα 76, and Dγ 77 from Aspergillus aculeatus [113], in addition to aculeacins B, C, D, E, F and G of which the structures have not been reported [114]; FR190293 81 and FR227673 85 from a Chalara species and from Tolypocladium parasiticum (now identified as Phialophora sp.) [115]; FR209602 82 from Coleophoma crateriformis [116]; FR901379 86 from Coleophoma empetri; mulundocandin 89 and desoxy-mulundocandin 90 from Aspergillus mulundensis [117]; pneumocandins A0-A4 91-95, B0 96, B2 97 and C0 98 from Zalerion arboricola, Glarea lozoyensis, and some Cryptosporiopsis sp.…”