Abstract:
:myo-Inositol (mI) is widely distributed in all domains of life and is important for several cellular functions, including bacterial survival. The enzymes responsible for the bacterial catabolism of mI, encoded in the iol operon, can vary from one organism to another, and these pathways have yet to be fully characterized. We previously identified a new scyllo-inositol dehydrogenase (sIDH) in the iol operon of Lactobacillus casei that can oxidize mI in addition to the natural substrate, scyllo-inositol, but the product of mI oxidation was not determined. Here we report the identification of these metabolites by monitoring the reaction with 13C nuclear magnetic resonance. We prepared all six singly 13C-labeled mI isotopomers through a biocatalytic approach and used these labeled inositols as substrates for sIDH. The use of all six singly labeled mI isotopomers allowed for metabolite characterization without isolation steps. sIDH oxidation of mI produces 1l-5-myo-inosose preferentially, but also two minor products, 1d-chiro-inosose and 1l-chiro-inosose. Together with previous crystal structure data for sIDH, we were able to rationalize the observed oxidation preference. Our relatively simple procedure for the preparation of isotopically labeled mI standards can have broad applications for the study of mI biotransformations.
journal_name
Biochemistryjournal_title
Biochemistryauthors
Ramos-Figueroa JS,Aamudalapalli HB,Jagdhane RC,Smith J,Palmer DRJdoi
10.1021/acs.biochem.0c00539subject
Has Abstractpub_date
2020-08-18 00:00:00pages
2974-2985issue
32eissn
0006-2960issn
1520-4995journal_volume
59pub_type
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