Specific and non-specific enzymes for furanosyl-containing conjugates: biosynthesis, metabolism, and chemo-enzymatic synthesis

The Impact of Recent Developments in Technologies which Enable the Increased Use of Biocatalysts

Complex molecules, clever solutions – Enzymatic approaches towards natural product and active agent syntheses

A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.

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Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine

Xylitol capric acid esters are widely applied due to their surfactant properties. In this study, site-specific xylitol dicaprate ester was obtained in a solvent-free system in the presence of lipase Candida sp. 99-125. UPLC-MS, and NMR analysis revealed that diesters were substituted at the C-1, C-5 positions. A series of experiments defined the optimum conditions of temperature, water content, loading of lipase, molar ratio and time course. The yield of xylitol esters reached 70% after 4 successive additions of xylitol. A subsequent coupling reaction and separation was introduced and significantly increased the yield of esters and also reduced the cost of the process. The lipase could be reused for 5 times with the yield of esters still reaching 50%.

Site-specific xylitol dicaprate ester synthesized by lipase from Candida sp. 99-125 with solvent-free system

Synthesis and Quantitative Analysis of Diastereomeric Linked Ester Conjugates With Remote Stereocenters Using High‐Field NMR and Chiral HPLC

An extension of the scope of the chemoenzymatic strategy for the synthesis of stereochemically pure pyranose deoxy sugar esters of different carboxylic acids has been achieved. The objective of the work was to extend the strategy to the synthesis of furanose deoxy sugar derivatives and additionally, to N-Boc-protected amino acid esters. With all used carboxylic acids (deoxycholic acid, α-methoxyphenylacetic acid, N-Boc- l -phenylalanine and N-Boc- l -tyrosine) the lipase-catalyzed stereoselective acetylation of furanose or pyranose hemiacetal moiety as a key step afforded one desired stereochemically pure acetylated hemiacetal deoxy sugar ester in high de.

A chemoenzymatic synthesis of deoxy sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB

This chapter contains sections titled: Production of Isorhamnetin 3-O-Glucoside in Escherichia coli Using Engineered Glycosyltransferase Multienzymatic Preparation of (−)-3-(Oxiran-2-yl)Benzoic Acid Enzymatic Synthesis of Carbohydrates from Dihydroxyacetone and Aldehydes by a One Pot Enzyme Cascade Reaction Aldolase Based Multi-Enzyme System for Carbon[BOND]Carbon Bond Formation Tandem Biocatalytic Process for the Kinetic Resolution of β-Phenylalanine and its Analogs A Chemoenzymatic Synthesis of a Deoxy Sugar Ester of N-Boc-Protected L-Tyrosine Electrochemical Systems for the Recovery of Succinic Acid from Fermentations

Tandem and Sequential Multi-Enzymatic Syntheses

Stereoselective Synthesis of γ‐(Acyloxy)Carboxylic Acids and γ‐Lactones Features the Switch of Stereopreference of CalB Along Sodium γ‐Hydroxycarboxylate Homologues

Marina Kudryashova

Papers

Synthesis and Quantitative Analysis of Diastereomeric Linked Ester Conjugates With Remote Stereocenters Using High‐Field NMR and Chiral HPLC

A chemoenzymatic synthesis of deoxy sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB

Tandem and Sequential Multi-Enzymatic Syntheses

Stereoselective Synthesis of γ‐(Acyloxy)Carboxylic Acids and γ‐Lactones Features the Switch of Stereopreference of CalB Along Sodium γ‐Hydroxycarboxylate Homologues