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(MK-641) is a potent irreversible inhibitor of alanine racemase7)8). We expected that it would inhibit the formation ofd-Ala within the producing culture and be incorporated in its place to form a fluorinated cyclosporin analog given the close isosteric similarities of fluorine and hydrogen atoms. In fact, as an antibacterial agent 2-2H-3-F-D-Ala was combined with the D-Ala-D-Ala ligase inhibitor pentizidone

The preparation of (2-deutero-3-fluoro-D-alA8)cyclosporin A by directed biosynthesis.