Chemo-enzymatic synthesis of chiral precursor molecules with chiral ring hydroxyenone and acetoxyenone structures

Hatice Becerekli; Şaziye Betül Sopacı

Makale detayları

Chemo-enzymatic synthesis of chiral precursor molecules with chiral ring hydroxyenone and acetoxyenone structures

Yazarlar:

Hatice Becerekli | Şaziye Betül Sopacı

Yayıncı:

Gültekin ÖZDEMİR

Ana Başlıklar:

Food Engineering | Food Biotechnology

Dergi:

International Journal of Agriculture Environment and Food Sciences Vol.7 Issue 2, pp.275-283

Belge Tipi:

Makale

Yayın Tarihi:

6/2023

Belge Dili:

İngilizce

Document ID (Org No.):

2001290035

pISSN:

2618-5946

Anahtar kelimeler:

Özet:

 A biocatalytic transformation has the potential to perform organic reactions that are quite challenging to achieve with synthetic organic chemistry. They also catalyze these reactions with a chemo and enantio selective manner. The discovery and development of new chemoenzymatic methods for the synthesis of these chiral structures is essential to the production of a wide range of bioactive compounds. In this study, two important pharmaceutical precursors were synthesized chemoenzymatically and subjected to biocatalytic conversions with different dehydrogenases. One of these compound is an α-acetoxy enone structure 4-methoxy-2-oxacyclohex-3-enyl acetate and the other is an α-hydroxy ketone 6-hydroxy-3-methoxycycyclohex-2-enone. To obtain these pharmaceutical precursors, 3-methoxy-cyclohex-2-enone was prepared using 1,3-diketone as a starting material. After obtaining this material, α-acetoxy enone was synthesized by chemical acetylation and α-hydroxy ketone prepared by enzymatic deacetylation. The structure of these products was elucidated by NMR analysis. In addition, biocatalytic reduction reactions involving the enzymes galactitol dehydrogenase GatDH, shikimate dehydrogenase SDH and diaphorase were carried out with these products.

 A biocatalytic transformation has the potential to perform organic reactions that are quite challenging to achieve with synthetic organic chemistry. They also catalyze these reactions with a chemo and enantio selective manner. The discovery and development of new chemoenzymatic methods for the synthesis of these chiral structures is essential to the production of a wide range of bioactive compounds. In this study, two important pharmaceutical precursors were synthesized chemoenzymatically and subjected to biocatalytic conversions with different dehydrogenases. One of these compound is an α-acetoxy enone structure 4-methoxy-2-oxacyclohex-3-enyl acetate and the other is an α-hydroxy ketone 6-hydroxy-3-methoxycycyclohex-2-enone. To obtain these pharmaceutical precursors, 3-methoxy-cyclohex-2-enone was prepared using 1,3-diketone as a starting material. After obtaining this material, α-acetoxy enone was synthesized by chemical acetylation and α-hydroxy ketone prepared by enzymatic deacetylation. The structure of these products was elucidated by NMR analysis. In addition, biocatalytic reduction reactions involving the enzymes galactitol dehydrogenase GatDH, shikimate dehydrogenase SDH and diaphorase were carried out with these products.

 A biocatalytic transformation has the potential to perform organic reactions that are quite challenging to achieve with synthetic organic chemistry. They also catalyze these reactions with a chemo and enantio selective manner. The discovery and development of new chemoenzymatic methods for the synthesis of these chiral structures is essential to the production of a wide range of bioactive compounds. In this study, two important pharmaceutical precursors were synthesized chemoenzymatically and subjected to biocatalytic conversions with different dehydrogenases. One of these compound is an α-acetoxy enone structure 4-methoxy-2-oxacyclohex-3-enyl acetate and the other is an α-hydroxy ketone 6-hydroxy-3-methoxycycyclohex-2-enone. To obtain these pharmaceutical precursors, 3-methoxy-cyclohex-2-enone was prepared using 1,3-diketone as a starting material. After obtaining this material, α-acetoxy enone was synthesized by chemical acetylation and α-hydroxy ketone prepared by enzymatic deacetylation. The structure of these products was elucidated by NMR analysis. In addition, biocatalytic reduction reactions involving the enzymes galactitol dehydrogenase GatDH, shikimate dehydrogenase SDH and diaphorase were carried out with these products.

 A biocatalytic transformation has the potential to perform organic reactions that are quite challenging to achieve with synthetic organic chemistry. They also catalyze these reactions with a chemo and enantio selective manner. The discovery and development of new chemoenzymatic methods for the synthesis of these chiral structures is essential to the production of a wide range of bioactive compounds. In this study, two important pharmaceutical precursors were synthesized chemoenzymatically and subjected to biocatalytic conversions with different dehydrogenases. One of these compound is an α-acetoxy enone structure 4-methoxy-2-oxacyclohex-3-enyl acetate and the other is an α-hydroxy ketone 6-hydroxy-3-methoxycycyclohex-2-enone. To obtain these pharmaceutical precursors, 3-methoxy-cyclohex-2-enone was prepared using 1,3-diketone as a starting material. After obtaining this material, α-acetoxy enone was synthesized by chemical acetylation and α-hydroxy ketone prepared by enzymatic deacetylation. The structure of these products was elucidated by NMR analysis. In addition, biocatalytic reduction reactions involving the enzymes galactitol dehydrogenase GatDH, shikimate dehydrogenase SDH and diaphorase were carried out with these products.

Makale detayları

Chemo-enzymatic synthesis of chiral precursor molecules with chiral ring hydroxyenone and acetoxyenone structures

Yazarlar:

Hatice Becerekli | Şaziye Betül Sopacı

Yayıncı:

Gültekin ÖZDEMİR

Ana Başlıklar:

Food Engineering | Food Biotechnology

Dergi:

International Journal of Agriculture Environment and Food Sciences Vol.7 Issue 2, pp.275-283

Belge Tipi:

Makale

Yayın Tarihi:

6/2023

Belge Dili:

İngilizce

Document ID (Org No.):

2001290035

pISSN:

2618-5946

Biotransformation

Lipase

Dehydrogenase

Acetoxygenone

α-hydroxyketonBiotransformation

Lipase

Dehydrogenase

Acetoxygenone

α-hydroxyketon

Sayı

Makale detayları

Yazarlar: Hatice Becerekli | Şaziye Betül Sopacı

Yayıncı: Gültekin ÖZDEMİR

Ana Başlıklar: Food Engineering | Food Biotechnology

Dergi: International Journal of Agriculture Environment and Food Sciences Vol.7 Issue 2, pp.275-283

Belge Tipi: Makale

Yayın Tarihi: 6/2023

Belge Dili: İngilizce

Document ID (Org No.): 2001290035

pISSN: 2618-5946

Sayı

Yazarlar:

Hatice Becerekli | Şaziye Betül Sopacı

Yayıncı:

Gültekin ÖZDEMİR

Ana Başlıklar:

Food Engineering | Food Biotechnology

Dergi:

International Journal of Agriculture Environment and Food Sciences Vol.7 Issue 2, pp.275-283

Belge Tipi:

Makale

Yayın Tarihi:

6/2023

Belge Dili:

İngilizce

Document ID (Org No.):

2001290035

pISSN:

2618-5946