Recent Advances in Aldolase-Catalyzed Synthesis of Unnatural Sugars and Iminocyclitols
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- Sugiyama Masakazu
- Ajinomoto . Co. Inc., Aminoscience Laboratories
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- Greenberg William
- Department of Chemistry , The Scripps Research Institute
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- Wong Chi-Huey
- Department of Chemistry , The Scripps Research Institute
Bibliographic Information
- Other Title
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- アルドラーゼを用いた糖類合成の展開
- アルドラーゼ オ モチイタ トウルイ ゴウセイ ノ テンカイ
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Abstract
Facile chemoenzymatic methods for the synthesis of a variety of D- and L- iminocyclitols or L-sugars have been developed. The practicality of formerly reported methods using dihydroxyacetone phosphate (DHAP) aldolase was limited by the high cost and instability of DHAP. Here we discuss three strategies toward the facile synthesis of sugar analogues using DHA(P) aldolases from readily available non-phosphoryrated donor substrates. (1) Directed evolution of the L-rhamnulose 1-phosphate aldolase (RhaD) was employed to alter the donor substrate specificity of RhaD aldolase from DHAP to DHA. In vivo selection for the directed evolution using genetically engineered E. coli strain was constructed . (2) RhaD aldolase was found to accept non-phosphorylated dihydroxyacetone (DHA) as a donor substrate in the presence of borate. We applied this discovery to develop a practical one-step synthesis of L-fructose and two-step synthesis of L-iminocyclitols . (3) A one-pot synthesis was achieved using the recently discovered D-fructose 6-phosphate aldolse (FSA). FSA utilized DHA, hydroxyacetone, and 1-hydroxy-2-butanone as donor substrates to allow the synthesis of a variety of novel D-iminocyclitols in a concise fashion.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 66 (6), 605-615, 2008
The Society of Synthetic Organic Chemistry, Japan
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Details 詳細情報について
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- CRID
- 1390001205310891136
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- NII Article ID
- 10021175615
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 9545078
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed