ISSN:
1435-1463
Keywords:
Biosynthesis of 1,4-benzodiazepines
;
endogenous benzodiazepines
;
deschlordiazepam
;
deschlor-nordiazepam
;
quinoline alkaloids
;
cyclopeptine
;
cyclopenin
;
viridicatin
;
ortho-aminobenzophenone
Source:
Springer Online Journal Archives 1860-2000
Topics:
Medicine
Notes:
Summary A first rational concept for the in vivo formation of naturally occurring diazepam-type 1,4-benzodiazepines is suggested — by oxidative carbon-carbon bond cleavage of the known quinoline alkaloid viridicatin, a fungal metabolite fromPenicillium species, replacement of the resultingN-oxaloyl substituent by a glycinoyl residue, and subsequent ring closure under Schiff base formation. In principle, all the proposed individual reaction steps as such are known from the literature: they have either been proven to occur in vivo, or they have been performed chemically. According to this concept, diazepam-type benzodiazepines would not only represent the joint result of both industrial developments and evolutionary processes in nature, but would even arise from identical precursors —ortho- aminobenzophenone and glycine! Alternatively, according to a slightly modified (more “economical”) biogenetic concept, the oxaloyl residue would not be substituted, but rather converted into the glycinoyl part. This hypothetic biosynthesis of naturally occurring 1,4-benzodiazepines might proceed in part in microorganisms (e.g. in fungi) and in part in higher organisms (e.g. in plants).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01245038
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