Infinity Supercritical LLC


Publication Title | Classic Terpene Syntheses

Cannabis Search Engine Series

Hops | Oil Extraction | Cultivation | Supercritical CO2 Fluid Extraction search was updated real-time via Filemaker on:

Hops | Oil Extraction | Cultivation | Supercritical CO2 Fluid Extraction | Return to Search List

Search Completed | Title | Classic Terpene Syntheses
Original File Name Searched: Maimone_Oct_05.pdf | Google It | Yahoo | Bing



Page Number: 001
Previous Page View | Next Page View

Text | Classic Terpene Syntheses | 001



Baran Lab Classic Terpene Syntheses

I. An Introduction to Terpenes

-Terpenes are an enormous class of natural products spanning well over 30,000 members

-They have been used throughout history for a broad variety of purposes including perfume, medicine, and flavoring -Recognized early on as being composed of isoprene fragments

-Isopentyl diphosphate (IPP) and dimethyl allyl diphosphate (DMAPP) later found to be the actual building blocks

-There are 2 biosynthetic pathways for the production of IPP and DMAPP, the mevalonate pathway and the more recently

Tom Maimone

discovered deoxyxylulose pathway

The Chemistry of the Mevalonate Pathway:

Isoprene

O

O

O

O

Aldoland

Hydrolysis HO2C

OH O

HMG-CoA

-CO2

OH OH

H SCoA

mevaldic acid hemithioacetal

OH

HO2C

mevaldic acid

SCoA SCoA

Claisen

SCoA

NADPH HO2C

SCoA

O

O

The Chemistry of the Deoxyxylulose Pathway:

OH P

O

acetyl-CoA

- Equilibrium favors DMAPP

acetoacetyl-CoA

SEnz

Isomerase

O

NADPH OH

O

HO P O ADP

OH OH OPP

OPP DMAPP

OPP

2xATP

OH OH OH OH

O OH

OPOO P

HO2C

mevalonic acid (MVA)

OH

IPP

O OH O OH

NH2 N

NO O

OH

O

O P O P O

Pinacol-type OP rearrangement

OH

OP O OH

NADPH

OH

OP OH OH

1. CTP

O

O OH

H+

1-deoxy-D-xylulose 5-P (from pyruvic acid)

2.ATP 2-C-methyl-D-erythritol 4-P

HO

OPP

Isomerase

OPP

steps not O fully determined OH OH

OH

DMAPP

IPP

* For an excellent review on natural products and biosynthesis see: Dewick, P.M. Medicinal Natural Products: A Biosynthetic Approach. Wiley, 2002.

1

Image | Classic Terpene Syntheses



classic-terpene-syntheses
Supercritical CO2 Fluid Extractor | Oil Extract Using Infinity Supercritical CO2 Extraction System - Botanical CO2 Extraction System - Go to website

Search Engine Contact: greg@infinitysupercritical.com