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Construction of a Highly Diastereoselective Aldol Reaction System with l-Threonine Aldolase by Computer-Assisted Rational Molecular Modification and Medium Engineering
- Source :
- Organic letters. 22(15)
- Publication Year :
- 2020
-
Abstract
- Diastereoselectivity of l-threonine aldolase (LTA) was determined by paths of aldehydes attacking a pyridoxal phosphate-glycine complex. Thus, strategies of enhancing the syn path and blocking the anti path were performed to modify LTA. A mutant (Y31H/N305R) was constructed with a substrate preference increase from 3.32 to 42.04. Medium engineering was investigated. Consequently, the de value of l-syn-3-[4-(methylsulfonyl)phenylserine] reached 93.1% (87.2%conv). The study clarified the factors affecting diastereoselectivity of LTA and provided a theorem for rational modification of LTA's diastereoselectivity.
- Subjects :
- Stereochemistry
Glycine
010402 general chemistry
01 natural sciences
Biochemistry
Substrate Specificity
chemistry.chemical_compound
Aldol reaction
Molecular modification
Escherichia coli
Serine
Physical and Theoretical Chemistry
Pyridoxal
Glycine Hydroxymethyltransferase
Aldehydes
biology
Molecular Structure
010405 organic chemistry
Computers
Organic Chemistry
Aldolase A
Substrate (chemistry)
Stereoisomerism
0104 chemical sciences
chemistry
Pyridoxal Phosphate
biology.protein
L-threonine
Subjects
Details
- ISSN :
- 15237052
- Volume :
- 22
- Issue :
- 15
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....068fd6bc9c56c4c7a1db7a3c2acdf9d6