Manool Production via Copalyl Diphosphate Synthase Pathway

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Solution Overview

Problem

Current methods for producing (+)-manool are inefficient, as they often result in small amounts as a by-product during sclareol production, and there is a need for a more effective biochemical pathway to isolate and produce this terpene.

Innovation Solution

The method involves contacting geranylgeranyl diphosphate with a copalyl diphosphate synthase to form (9S, 10S)-copalyl diphosphate, followed by conversion with a sclareol synthase to produce (+)-manool, using enzymes with specific amino acid sequences that have high identity to SEQ ID NO: 1 and SEQ ID NO: 2, and optionally isolating the (+)-manool.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If sclareol production is performed using labdenyl diphosphate synthase and sclareol synthase, then sclareol is produced, but only small amounts of (+)-manool are obtained as a by-product

Engineering Contradiction:
Improveamount of (+)-manoolVSAvoidproduction efficiency of (+)-manool
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

The patent extracts and isolates the specific enzymatic pathway for (+)-manool production by using copalyl diphosphate synthase to selectively produce copalyl diphosphate as a separate step, which is then converted to (+)-manool by sclareol synthase. This separates the (+)-manool production pathway from the sclareol production pathway, allowing focused optimization of (+)-manool yields without being limited to trace by-product formation.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the substrate parameters by using geranylgeranyl diphosphate (GGPP) as the starting material and copalyl diphosphate synthase to produce copalyl diphosphate with specific stereochemistry ((9S,10S)-configuration). This parameter change in substrate structure and enzyme specificity enables high-yield (+)-manool production rather than trace by-product formation.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If copalyl diphosphate synthase from Salvia miltiorrhiza is used, then copalyl diphosphate is formed, but the production of (+)-manool requires additional optimization

Engineering Contradiction:
Improveamount of copalyl diphosphateVSAvoidprocess complexity for (+)-manool production
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent performs preliminary action by first using copalyl diphosphate synthase to produce copalyl diphosphate, which is then used as the substrate for sclareol synthase to produce (+)-manool. This two-step preliminary enzymatic preparation simplifies the overall process by breaking down the complex transformation into manageable stages with optimized intermediates.

Inventive Principle:
Principle #10Preliminary action

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach allows for the efficient production of (+)-manool with high purity, achieving yields of at least 98% and enabling the derivation of various manool derivatives, such as manool acetate and copalol, through enzymatic or chemical processes.

Implementation Method 1

contacting geranylgeranyl diphosphate with a copalyl diphosphate synthase to form a (9S, 10S)-copalyl diphosphate

Methodology Applied
Scientific EffectEnzyme catalysis: Enzyme

Implementation Method 2

contacting the (9S, 10S)-copalyl diphosphate CPP with a sclareol synthase to form (+)-manool

Methodology Applied
Scientific EffectEnzyme catalysis: Enzyme

Data Source

PatentEP3317418B1Production of manool
Publication Date: 2022.11.30 FIRMENICH SA
  • EP3317418B1 patent drawingFigure 1
  • EP3317418B1 patent drawingFigure 2A~2C
  • EP3317418B1 patent drawingFigure 3A~3D

AI summary

Provided herein are methods of producing (+)-manool comprising: contacting geranylgeranyl diphosphate with an copalyl diphosphate (CPP) synthase to form a (9S, 10S)-copalyl diphosphate wherein the CPP synthase comprises an amino acid sequence having at least 90%, 95%, 98%), 99% and 100% sequence identity to a polypeptide selected from the group consisting of SEQ ID NO: 1 and SEQ ID NO:2; and contacting the CPP with a sclareol synthase enzyme to form (+)-manool.