7776-21-8Relevant academic research and scientific papers
The Biosynthetic Incorporation of Phenylalanine into Gliotoxin
Johns, Nicholas,Kirby, Gordon W.
, p. 1487 - 1490 (2007/10/02)
When mixtures of DL--m-tyrosine and DL-phenylalanine were fed to cultures of Gliocladium deliquescens good incorporation (4.9 and 1.6percent in separate experiments) of (14)C and negligible incorporation (ca. 0.04percent) of (3)H into the derived gliotoxin (2) was observed.Incorporation of DL--, DL--, and L--phenylalanine into gliotoxin occured without loss of tritium.Degradation of the gliotoxin gave, in each case, bis(anhydro-dethio)gliotoxin (3) and dehydrogliotoxin (4) having a tritium content indicating that the incorporation of phenylalanine had occured without migration of tritium.These results, taken together, show that neither m-tyrosine (3'-hydroxyphenylalanine) nor any other hydroxybenzene derivative can be an obligatory intermediate on the biosynthetic pathway from phenylalanine to gliotoxin.The possible involvement of arene oxides in gliotoxin biosyhthesis is discussed.
TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN
Fukuyama, Tohru,Nakatsuka, Shin-Ichi,Kishi, Yoshito
, p. 2045 - 2078 (2007/10/02)
Two general methods, Method A and Method B in Scheme 19, to synthesize epidithiapiperazinediones, are described.A total synthesis of racemic and optically active gliotoxin (1) and of racemic dehydrogliotoxin (53) was achieved by using Method A, whereas a total synthesis of racemic hyalodendrin (52) was completed by using Method B.
