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- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/27%3A_Biomolecules_-_Lipids/27.08%3A_Biosynthesis_of_SteroidsThe mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydrope...The mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydroperoxide oxygen. Thus, each 1,2-hydride or 1,2-methyl shift occurs to the backside of the orbital connected to the leaving group in what can be viewed as a series of nucleophilic substitution reactions – where σ-bonding electron pairs serve as the nucleophiles.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/13%3A_Biomolecules_-_Lipids/13.08%3A_Biosynthesis_of_SteroidsThe mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydrope...The mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydroperoxide oxygen. Thus, each 1,2-hydride or 1,2-methyl shift occurs to the backside of the orbital connected to the leaving group in what can be viewed as a series of nucleophilic substitution reactions – where σ-bonding electron pairs serve as the nucleophiles.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/27%3A_Biomolecules_-_Lipids/27.08%3A_Biosynthesis_of_SteroidsThe proposed mechanism involves reaction of FADH 2 with O 2 to produce a flavin hydroperoxide intermediate (ROOH), which transfers an oxygen to squalene in a pathway initiated by nucleophilic attack o...The proposed mechanism involves reaction of FADH 2 with O 2 to produce a flavin hydroperoxide intermediate (ROOH), which transfers an oxygen to squalene in a pathway initiated by nucleophilic attack of the squalene double bond on the terminal hydroperoxide oxygen (Figure 27.14). In step 6, a second hydride migration occurs from C13 to C17 on the α (bottom) face of the ring and reestablishes the 17β orientation of the side chain.
- https://chem.libretexts.org/Courses/Martin_Luther_College/Organic_Chemistry_-_MLC/05%3A_Biomolecules/5.03%3A_Biomolecules_-_Lipids/5.3.08%3A_Biosynthesis_of_SteroidsThe mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydrope...The mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydroperoxide oxygen. Thus, each 1,2-hydride or 1,2-methyl shift occurs to the backside of the orbital connected to the leaving group in what can be viewed as a series of nucleophilic substitution reactions – where σ-bonding electron pairs serve as the nucleophiles.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_III_(Morsch_et_al.)/27%3A_Lipids/27.07%3A_Biosynthesis_of_SteroidsThe mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydrope...The mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydroperoxide oxygen. Thus, each 1,2-hydride or 1,2-methyl shift occurs to the backside of the orbital connected to the leaving group in what can be viewed as a series of nucleophilic substitution reactions – where σ-bonding electron pairs serve as the nucleophiles.
- https://chem.libretexts.org/Courses/Williams_School/Chemistry_II/08%3A_Biomolecules_-_Lipids/8.07%3A_Biosynthesis_of_SteroidsThe mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydrope...The mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydroperoxide oxygen. Thus, each 1,2-hydride or 1,2-methyl shift occurs to the backside of the orbital connected to the leaving group in what can be viewed as a series of nucleophilic substitution reactions – where σ-bonding electron pairs serve as the nucleophiles.
