Echinocandin B

Synthesis of deuteriated and tritiated echinocandin B and anilinostearamide and the problem of HPLC isotope effects... 

Echinocandins B-D -lipopeptide antibiotics and other peptides including aculeacin A, mulundocandin, and pneumocandins... 

Anidulafimgin (23 Echinocandin B (24) Lipopeptide Semi-synthetic Microbial Antifungal Inhibits fungal cell wall 279-293... 

One example of the utilization of this approach for the synthesis of natural products is the facile access, Fig. 10, to the southwest tripeptide segment of echinocandin B, 148, a cyclic hexapeptide that is characterized by its antifungal and antiyeast activity. 

Fig. 10 Structure of echinocandin B which shows antifungal and antiyeast activity...

M Debono, BJ Abbott, DS Fukuda, M Barnhart, KE Willard, RM Molloy, KM Michel, JR Turner, TF Butler, AH Hunt. Synthesis of new analogs of echinocandin B by enzymatic deacylation and chemical reacylation of the echinocandin B peptide synthesis of the antifungal agent cilofungin (LY121019). J Antibiot 42 389-397, 1988. 

M Debono, BJ Abbott, JR Turner, LC Howard, RS Gordee, AS Hunt, M Barnhart, RM Molloy, KE Willard, DS Fukuda, TF Butler, DJ Zeckner. Synthesis and evaluation of LY121019, a member of a series of semisynthetic analogues of the antifungal lipopeptide echinocandin B. Ann NY Acad Sci 544 152-167, 1988. 

JA Jamison, DJ Zeckner, MJ Rodriguez. The synthesis and antifungal activity of V-alkylated analogs of echinocandin B. J. Antibiot 50 562-566, 1997. 

W Pache, C Keller, M Kuhn. Cleavage of echinocandin B with polymyxin acylase liberating the fatty acid and reacylation of the peptide moiety. Experientia 34 1670-1671, 1978. 

LD Boeck, DS Fukuda, BJ Abbott, M Debono. Deacylation of echinocandin B by Actinoplanes utahensis. J Antibiot 42 382-388, 1989. 

AJ Kreuzman, RL Hodges, JR Swartling, TE Pohl, SK Ghag, PJ Baker, D McGil-vray, WK Yeh. Membrane-associated echinocandin B deacylase of Actinoplanes utahensis. purification, characterization, heterologous cloning and enzymatic deacylation reaction. J Ind Microbiol Biotechnol 24 173-180, 2000. 

AR Cockshott, GR Sullivan. Improving the fermentation medium for echinocandin B production Part I sequential statistical experiment design. Process Biochem 36 647-660, 2001. 

Echinocandin B Sandoz Ciba-Geigy Lilly OH OH OH ch3 ch3 Linoleic acid... 

In the 1970s scientists at Eli Lilly Co. determined that echinocan-din B had potent antifungal activity against C. albicans and Candida trop-icalis and in vivo activity in animal models of candidiasis. Its limitations for human therapeutics were lack of oral bioavailability and poor water solubility. There was also concern because it produced in vitro lysis of red blood cells. Early chemical modifications focused on reducing the lytic potential of echinocandin B and showed that the fatty acyl tail... 

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