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O'Connor - Alkaloid Biosynthesis Nitrogen containing...

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Starting materials: Amino acids and nucleic acids NMe HN OH O H H N N N N O O CH 3 CH 3 H 3 C N Me O CO 2 Me O pseudopelletierine nicotine N N Me H caffeine ergot O NCH 3 HO HO H H morphine CO 2 NH 3 OH N H NH 3 CO 2 N N N N NH 2 O OH OH O P -O O - O NH 3 CO 2 H 3 N CO 2 H 3 N NH 3 N Me O cocaine ornithine purine tyrosine lysine tryptophan Alkaloid Biosynthesis: Nitrogen containing compounds S. O’Connor Biochemistry 704 2/5/08 ajmaline N H NH 3 CO 2 tryptophan N Me N OH HO H O O HO O OH OCH 3 O HO HO OH O O HO O OH HO OH HO Endogenous Roles of Natural Products insecticide attraction signalling UV-protectants N N N N O O CH 3 CH 3 H 3 C N N Me H N N OH OH O HO OH O OH antibiotic/antifungal O Cl H 3 CO Cl OH HO NO 2 HO NH CHCl 2 OH O scent color S. O’Connor Biochemistry 704 2/5/08 Endogenous Roles of Natural Products alkaloids made by plants fungi bacteria S. O’Connor Biochemistry 704 2/5/08 NMe HN OH O H H N Me O CO 2 Me O ergot cocaine Tetrahydroisoquinoline Biosynthesis S. O’Connor Biochemistry 704 2/5/08 NH 2 O HO HO HO NH HO HO HO H NH H 3 CO HO HO H 6-OMT NCH 3 H 3 CO HO HO H NCH 3 H 3 CO HO H 3 CO H N OH OCH 3 H 3 CO HO NCH 3 H 3 CO H O H 3 CO NCH 3 H 3 CO HO HO H HO HO CPY80B3 NCS 4OMT BBE berberine sanguinarine N + O O O O N + O O OMe OMe L-tyrosine NCH 3 O H O H 3 CO NCH 3 H 3 CO HO H 3 CO HO H NCH 3 H 3 CO H HO H 3 CO O NCH 3 H 3 CO H HO H 3 CO HO NCH 3 H 3 CO H HO H 3 CO HO H STS SOR SAT spontaneous NCH 3 H O H 3 CO NCH 3 HO H O HO HO COR H H H codeinone thebaine salitidarol-7-O-acetate salutaridinol salutaridine (R)-reticuline codeine morphine NCH 3 O H O H 3 CO HO oxycodone NCH 3 + H 3 CO HO H 3 CO HO 1,2-dehydroreticuline (S)-scoulerine (S)-norcoclaurine (S)-reticuline morphanan type benzophenanthridine type berberine type NMT
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