# US 5,352,591 A · Aldolase enzyme process for making 5-azido-5-deoxy-hexulose-1-phosphate

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- Number: US 5,352,591 A
- Document ID: US5352591A
- Status: Granted
- Kind: A
- Application number: 08/093,782
- Filed: 1993-07-19
- Granted: 1994-10-04
- Earliest claimed: 1991-05-30
- Assignees: The Scripps Research Institute
- Inventors: Chi-Huey Wong; Kun-Chin Liu
- Web page: https://patentgrep.com/patent/US5352591A

## CPC

- C07D 207/46: with hetero atoms directly attached to the ring nitrogen atom
- C07D 207/12: Oxygen or sulfur atoms
- C07H 7/02: Acyclic radicals
- C07H 11/00: Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof (halo-sugars C07H5/02; thio-, seleno-, or telluro-sugars C07H5/08)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

2-Methyl-5-hydroxymethyl-and 2,5-dimethyl-3,4-dihydroxypyrrolidines, their processes of preparation and use are disclosed. 5-Azido-5-deoxy-hexulose-1-phosphate compounds and processes of making the same are also disclosed.

## Claims

### Claim 1

A process of making a 5-azido-5-deoxyhexulose-1-phosphate comprising mixing a 2-azido-substituted-propionaldehyde and dihydroxyacetone phosphate in the presence of a catalytic amount of an aldolase to form a reaction mixture and maintaining the reaction mixture under biological reaction conditions for a time period sufficient to form said 5-azido-5-deoxy-hexulose-1-phosphate.

### Claim 2 (depends on 1)

The process according to claim 1 wherein the 2-azido-substituted-propionaldehyde is 2-azido-3-hydroxy-propanal and the formed compound is 5-azido-5-deoxy-L-xylo-hexulose-1-phosphate.

### Claim 3 (depends on 1)

The process according to claim 1 wherein the 2-azido-substituted-propionaldehyde is 2-azidopropanal and the formed compound is 5-azido-5,6-dideoxy-L-xylo-hexulose-1-phosphate.

### Claim 4 (depends on 1)

The process according to claim 1 including the further step of recovering said 5-azido-5-deoxy-hexulose-1-phosphate.

### Claim 5 (depends on 1)

The process according to claim 1 wherein the aldolase is selected from the group consisting of fructose-1,6-diphosphate aldolase, rhamnulose-1-phosphate aldolase, fuculose-1-phosphate aldolase and tagatose-1,6-diphosphate aldolase.

### Claim 6

A process of making a 5-azido-5-deoxy-hexulose-1-phosphate comprising mixing a 2-azido-substituted-propionaldehyde and dihydroxyacetone phosphate in the presence of a catalytic amount of an aldolase that is selected from the group consisting of fructose-1,6-diphosphate aldolase, rhamnulose-1-phosphate aldolase, fuculose-1-phosphate aldolase and tagatose-1,6-diphosphate aldolase to form a reaction mixture and maintaining the reaction mixture under biological reaction conditions for a time period sufficient to form said 5-azido-5-deoxy-hexulose-1-phosphate.