An update of biocatalytic selective acylation and deacylation of monosaccharides

Iribarren, Adolfo M.; Iglesias, Luis E.

doi:10.1039/c5ra23453k

Cited by 13 publications

(9 citation statements)

References 139 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[ 109 , 110 ]. These aspects must be taken into account in API synthesis processes (or their building blocks) that generally contain adjacent –OH groups, as in the case of the presence of sugars and their derivatives [ 111 , 112 ] and in other polyols: an example is the case of derivatives of Flurbiprofenate, a powerful nonsteroidal anti-inflammatory drug (NSAIDs), which has been esterified with L-ascorbic acid (a polyhydroxy acid) through the use of different lipases (CRL, PPL and Novozym ® 435) in order to improve its absorption in the brain [ 113 ].…”

Section: Microbial Lipases: Structure and Functionmentioning

confidence: 99%

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Godoy

Pardo‐Tamayo

Barbosa

2022

IJMS

View full text Add to dashboard Cite

Processes involving lipases in obtaining active pharmaceutical ingredients (APIs) are crucial to increase the sustainability of the industry. Despite their lower production cost, microbial lipases are striking for their versatile catalyzing reactions beyond their physiological role. In the context of taking advantage of microbial lipases in reactions for the synthesis of API building blocks, this review focuses on: (i) the structural origins of the catalytic properties of microbial lipases, including the results of techniques such as single particle monitoring (SPT) and the description of its selectivity beyond the Kazlauskas rule as the “Mirror-Image Packing” or the “Key Region(s) rule influencing enantioselectivity” (KRIE); (ii) immobilization methods given the conferred operative advantages in industrial applications and their modulating capacity of lipase properties; and (iii) a comprehensive description of microbial lipases use as a conventional or promiscuous catalyst in key reactions in the organic synthesis (Knoevenagel condensation, Morita–Baylis–Hillman (MBH) reactions, Markovnikov additions, Baeyer–Villiger oxidation, racemization, among others). Finally, this review will also focus on a research perspective necessary to increase microbial lipases application development towards a greener industry.

show abstract

Section: Microbial Lipases: Structure and Functionmentioning

confidence: 99%

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Godoy

Pardo‐Tamayo

Barbosa

2022

IJMS

View full text Add to dashboard Cite

show abstract

“…Recently, 6-O-acetylation by migration of acetyl group from O-2 has been developed. 39 Enzymatic acetylation [40][41][42] has also been applied for the selective introduction of acetyl groups at primary hydroxy groups of sugars.…”

Section: Introductionmentioning

confidence: 99%

Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Two carbohydrates, 2-Deoxy-2-(methacryloylamino)-D-glucopyranose and the ester 6-O-Acetyl-D-glucose, were upregulated following nutrient treatment. Carbohydrates exert important biochemical functions (energy supply, molecular recognition processes, structural roles, cell-surface functions) and are precursors of various molecules, particularly bioactive compounds, such as oligosaccharides, glycol-conjugates, and nucleosides [ 63 ].…”

Section: Discussionmentioning

confidence: 99%

Mixtures of Macro and Micronutrients Control Grape Powdery Mildew and Alter Berry Metabolites

Gur

Cohen

Frenkel

et al. 2022

Plants

View full text Add to dashboard Cite

Powdery mildew caused by the fungus Erysiphe necator is a major grape disease worldwide. It attacks foliage and berries and reduces yield and wine quality. Fungicides are mainly used for combating the disease. Fungicide resistance and the global requisite to reduce pesticide deployment encourage the use of environment-friendly alternatives for disease management. Our field experiments showed that the foliar application of the potassium phosphate fertilizer Top-KP+ (1-50-33 NPK) reduced disease incidence on leaves and clusters by 15–65% and severity by 75–90%, compared to untreated vines. Top-KP+ mixed with Nanovatz (containing the micronutrients boron (B) and zinc (Zn)) or with TruPhos Platinum (a mixture containing N, P2O5, K2O, Zn, B, Mg, Fe, Mn, Cu, Mo, and CO) further reduced disease incidence by 30–90% and disease severity by 85–95%. These fertilizers were as effective as the fungicide tebuconazole. Tank mixtures of fertilizers and tebuconazole further enhanced control efficacy in the vineyards. The modes of action of fertilizers in disease control were elucidated via tests with grape seedlings, microscopy, and berry metabolomics. Fertilizers applied preventively to the foliage of grape seedlings inhibited powdery mildew development. Application onto existing mildew colonies plasmolyzed mycelia and conidia and arrested the development of the disease. Berries treated with fertilizers or with a fungicide showed a significant increase in anti-fungal and antioxidant metabolites. Twenty-two metabolites, including non-protein amino acids and carbohydrates, known for their anti-fungal and bioactive effects, were significantly upregulated in grapes treated with fertilizers as compared to grapes treated with a fungicide, suggesting possible indirect activity against the pathogen. Esters and organic acids that contribute to wine quality were also upregulated. We conclude that integrating macro and micronutrients in spray programs in commercial vineyards shall control powdery mildew, reduce fungicide deployment, delay the buildup of fungicide resistance, and may improve wine quality.

show abstract

An update of biocatalytic selective acylation and deacylation of monosaccharides

Abstract: PAMs synthesis requires highly selective reactions, provided by hydrolases. This review updates research on enzymatic acylation and deacylation of monosaccharides, focusing on synthetic useful PAMs and drug-monosaccharide conjugates involving PAMs.

Cited by 13 publications

References 139 publications

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid

Mixtures of Macro and Micronutrients Control Grape Powdery Mildew and Alter Berry Metabolites

Contact Info

Product

Resources

About