Step 1 involves the hydroxylation of cycloheptane to cycloheptanol, catalyzed by enzyme p450 in the presence of the endogenous cofactor NADPH. Step 2 involves the oxidation of cycloheptanol to cycloheptanone, catalyzed by alcohol dehydrogenase (ADH) in the presence of NADP+, followed by the conversion of cycloheptanone to heptanolide by Baeyer-Villiger oxidase (BVMO). Heptanolide is then hydrolyzed by lactonease (Lac) to 7-hydroxyheptanoic acid, which is subsequently reduced to 1,7-heptanediol by CAR (with the aid of phosphoethyl ester transferase (SFP)) and endogenous aldehyde-ketone reductase (AKR). Step 3 involves two rounds of oxidation/amination reactions catalyzed by ChnD and TA: first, 1,7-heptanediol is oxidized to 7-hydroxyheptanal by ChnD, then amination with TA to 7-aminoheptanol, then oxidized again by ChnD to 7-aminoheptanal, and finally amination with TA to 1,7-diaminoheptane.
1,7-Diaminoheptane is used in the preparation of 7-amino-1-guanidinooctane and 1,7-diamino-trans-hept-3-ene, which is used as a deoxyhypusine synthase inhibitor.
