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Article; Pharmaceutical Biotechnology

Fungal biotransformation of ezetimibe

Irfan PervaizDepartment of Pharmacy, COMSATS Institute of Information Technology, AbbottabadPakistan;Faculty of Pharmacy and Alternative Medicine, Islamia University of Bahawalpur, BahawalpurPakistan

Saeed AhmadFaculty of Pharmacy and Alternative Medicine, Islamia University of Bahawalpur, BahawalpurPakistan

Farhan Hameed KhaliqFaculty of Pharmacy and Alternative Medicine, Islamia University of Bahawalpur, BahawalpurPakistan

Adeel ArshadDepartment of Pharmacy, COMSATS Institute of Information Technology, AbbottabadPakistan

Muhammad ImranDepartment of Pharmacy, COMSATS Institute of Information Technology, AbbottabadPakistan

Barkat Ali KhanDepartment of Pharmacy, Gomal University, Dera Ismail Khan, Pakistan

Aftab UllahDepartment of Pharmacy, COMSATS Institute of Information Technology, AbbottabadPakistan

Usman AliDepartment of Pharmacy, COMSATS Institute of Information Technology, AbbottabadPakistan

Kashif IqbalFaculty of Pharmacy, University of Balochistan, Quetta, Pakistan

Muhammad UsmanDepartment of Pharmacy, Abasyn University, Peshawar, Pakistan

Hafsa BibiDepartment of Chemistry, Gomal University, Dera Ismail Khan, Pakistan

Najm Ul Hassan KhanIslam College of Pharmacy, Sialkot, Pakistan

Wajahat MahmoodDepartment of Pharmacy, COMSATS Institute of Information Technology, AbbottabadPakistanCorrespondence[email protected]

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Table 1. Compound (1). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of ezetimibe (1) (3R, 4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl) azetidin-2-one (1).

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Table 2. Compound (2). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-((E)-3-(4-fluorophenyl) allyl)-4-(4-hydroxyphenyl) azetidin-2-one (2).

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Table 3. Compound (3). H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl) azetidin-2-one (3).

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Table 4. Compound (4). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S) 1-(4-fluorophenyl)-3-(3-(4-fluorophenyl) propyl)-4-(4-hydroxyphenyl) azetidin-2-one (4).

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Table 5. Compound (5). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (2R,5S)-N, 5-bis (4-fluorophenyl)-5-hydroxy-2-(4-hydroxybenzyl) pentanamide (5).

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Figure 1. Biotransformation of ezetimibe (1) by Beauvaria bassiana into compound (2) and compound (3).

Figure 2. Biotransformation of ezetimibe (1) by Cunninghamella blakesleeana into compound (4) and compound (5).

Fungal biotransformation of ezetimibe

Table 1. Compound (1). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of ezetimibe (1) (3R, 4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl) azetidin-2-one (1).

Table 2. Compound (2). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-((E)-3-(4-fluorophenyl) allyl)-4-(4-hydroxyphenyl) azetidin-2-one (2).

Table 3. Compound (3). H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl) azetidin-2-one (3).

Table 4. Compound (4). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S) 1-(4-fluorophenyl)-3-(3-(4-fluorophenyl) propyl)-4-(4-hydroxyphenyl) azetidin-2-one (4).

Table 5. Compound (5). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (2R,5S)-N, 5-bis (4-fluorophenyl)-5-hydroxy-2-(4-hydroxybenzyl) pentanamide (5).

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Fungal biotransformation of ezetimibe

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Table 1. Compound (1). 1H-NMR (100 MHz, CDCl3) and 13C-NMR (600 MHz, CDCl3) chemical shift assignments of ezetimibe (1) (3R, 4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl) azetidin-2-one (1).

Table 2. Compound (2). 1H-NMR (100 MHz, CDCl3) and 13C-NMR (600 MHz, CDCl3) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-((E)-3-(4-fluorophenyl) allyl)-4-(4-hydroxyphenyl) azetidin-2-one (2).

Table 3. Compound (3). H-NMR (100 MHz, CDCl3) and 13C-NMR (600 MHz, CDCl3) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl) azetidin-2-one (3).

Table 4. Compound (4). 1H-NMR (100 MHz, CDCl3) and 13C-NMR (600 MHz, CDCl3) chemical shift assignments of (3R,4S) 1-(4-fluorophenyl)-3-(3-(4-fluorophenyl) propyl)-4-(4-hydroxyphenyl) azetidin-2-one (4).

Table 5. Compound (5). 1H-NMR (100 MHz, CDCl3) and 13C-NMR (600 MHz, CDCl3) chemical shift assignments of (2R,5S)-N, 5-bis (4-fluorophenyl)-5-hydroxy-2-(4-hydroxybenzyl) pentanamide (5).

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Table 1. Compound (1). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of ezetimibe (1) (3R, 4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl) azetidin-2-one (1).

Table 2. Compound (2). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-((E)-3-(4-fluorophenyl) allyl)-4-(4-hydroxyphenyl) azetidin-2-one (2).

Table 3. Compound (3). H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl) azetidin-2-one (3).

Table 4. Compound (4). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (3R,4S) 1-(4-fluorophenyl)-3-(3-(4-fluorophenyl) propyl)-4-(4-hydroxyphenyl) azetidin-2-one (4).

Table 5. Compound (5). ¹H-NMR (100 MHz, CDCl₃) and ¹³C-NMR (600 MHz, CDCl₃) chemical shift assignments of (2R,5S)-N, 5-bis (4-fluorophenyl)-5-hydroxy-2-(4-hydroxybenzyl) pentanamide (5).