Biosynthesis of an unusual amino acyl moiety contained in bestatin.
The biosynthetic pathway of an unusual amino acyl [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl (AHP)] moiety which is contained in bestatin has been studied by testing the incorporation of potential precursors. L-[U-14C]-Phenylalanine, L-[U-14C]leucine, and [U-14C]acetic acid were efficiently incorporated into bestatin, but the radioactivity of L-[1-14C]phenylalanine, [1-14C]glyoxylic acid, and [14C]oxalic acid were not incorporated. Incorporation of acetic acid into 1- and 2-carbon of the AHP moiety was confirmed by incorporation of [13C]acetic acid. Thus, the AHP moiety was shown to be biosynthesized from L-phenylalanine and two carbon atoms of acetic acid, accompanied by decarboxylation of the phenylalanine.
D000085:Acetates / Q000378:metabolism; D019342:Acetic Acid; D000596:Amino Acids / Q000096:biosynthesis*; D000626:Aminopeptidases / Q000378:metabolism; D003653:Decarboxylation; D007930:Leucine / Q000031:analogs & derivatives* / Q000096:biosynthesis; D009682:Magnetic Resonance Spectroscopy; D010649:Phenylalanine / Q000378:metabolism; D013302:Streptomyces / Q000201:enzymology; D013997:Time Factors
D000085:Acetates; D000596:Amino Acids; D010649:Phenylalanine; D000626:Aminopeptidases; D007930:Leucine; C012211:ubenimex; D019342:Acetic Acid