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User:Benjah-bmm27/degree/3/RJC

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Natural products, RJC

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Examples of natural products

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Origin of natural products: secondary metabolism

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Themes

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Biological methylation

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Examples of key experiments in biosynthesis

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Radiolabelling

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Non-ribosomal peptide biosynthesis

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  • Thioesterases (TE) release acyl groups bound to enzymes as thioesters by simple hydrolysis
    • Enz-S-C(=O)-R + H2O –[TE]→ Enz-SH + RCO2H

Polyketide biosynthesis

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Lovastatin biosynthesis

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Terpene biosynthesis

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Alkaloid biosynthesis

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Alkaloids all contain a basic nitrogen atom. Their names end in -ine.

Examples of alkaloids

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Morphine biosynthesis

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  • (R)-reticuline from (S)-norcoclaurine
    • (S)-norcoclaurine –[O-methyl transferase, SAM]→ methoxy –[N-methyl transferase, SAM]→ N-methyl –[O]→ benzenediol –[O-Me Tf, SAM]→ (S)-reticuline
    • (S)-reticuline –[O]→ iminium –[NADPH]→ (R)-reticuline
  • Morphine from (R)-norcoclaurine
    • (R)-reticuline –[P450, O, remove 2H]→ salutaridine (radical mechanism)
    • salutaridine –[NADPH]→ salutaridinolthebaine
    • thebaine –[oxidative demethylation then rearrangement]→ codeinone
    • codeinone –[NADPH]→ –[oxidative demethylation]→ morphine

Pictet-Spenglerase

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Cocaine biosynthesis

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