Synthesis of a novel fluorinated phosphonyl C-glycoside, (3-deoxy-3-fluoro- β-d-glucopyranosyl)methylphosphonate, a potential inhibitor of β-phosphoglucomutase
Carbohydr Res. 2023 Nov 2;534:108979. doi: 10.1016/j.carres.2023.108979. Online ahead of print.ABSTRACTβ-phosphoglucomutase (βPGM) catalyzes the conversion of β-glucose 1-phosphate (βG1P) to glucose-6-phosphate (G6P), a universal source of cellular energy, in a two-step process. Transition state analogue (TSA) complexes formed from substrate analogues and a metal fluoride (MgF3- and AlF4-) enable analysis of each of these enzymatic steps independently. Novel substrate analogues incorporating fluorine offer opportunities to interrogate the enzyme mechanism using 19F NMR spectroscopy. Herein, the synthesis of a novel flu...
Source: Carbohydrate Research - November 6, 2023 Category: Genetics & Stem Cells Authors: Madison Carroll-Poehls David L Jakeman Source Type: research
Synthesis of a novel fluorinated phosphonyl C-glycoside, (3-deoxy-3-fluoro- β-d-glucopyranosyl)methylphosphonate, a potential inhibitor of β-phosphoglucomutase
Carbohydr Res. 2023 Nov 2;534:108979. doi: 10.1016/j.carres.2023.108979. Online ahead of print.ABSTRACTβ-phosphoglucomutase (βPGM) catalyzes the conversion of β-glucose 1-phosphate (βG1P) to glucose-6-phosphate (G6P), a universal source of cellular energy, in a two-step process. Transition state analogue (TSA) complexes formed from substrate analogues and a metal fluoride (MgF3- and AlF4-) enable analysis of each of these enzymatic steps independently. Novel substrate analogues incorporating fluorine offer opportunities to interrogate the enzyme mechanism using 19F NMR spectroscopy. Herein, the synthesis of a novel flu...
Source: Carbohydrate Research - November 6, 2023 Category: Genetics & Stem Cells Authors: Madison Carroll-Poehls David L Jakeman Source Type: research
Synthesis of a novel fluorinated phosphonyl C-glycoside, (3-deoxy-3-fluoro- β-d-glucopyranosyl)methylphosphonate, a potential inhibitor of β-phosphoglucomutase
Carbohydr Res. 2023 Nov 2;534:108979. doi: 10.1016/j.carres.2023.108979. Online ahead of print.ABSTRACTβ-phosphoglucomutase (βPGM) catalyzes the conversion of β-glucose 1-phosphate (βG1P) to glucose-6-phosphate (G6P), a universal source of cellular energy, in a two-step process. Transition state analogue (TSA) complexes formed from substrate analogues and a metal fluoride (MgF3- and AlF4-) enable analysis of each of these enzymatic steps independently. Novel substrate analogues incorporating fluorine offer opportunities to interrogate the enzyme mechanism using 19F NMR spectroscopy. Herein, the synthesis of a novel flu...
Source: Carbohydrate Research - November 6, 2023 Category: Genetics & Stem Cells Authors: Madison Carroll-Poehls David L Jakeman Source Type: research
Synthesis and characterization of novel chitosan derivatives (containing dipyridinium quaternary salts) with antimicrobial potential
In this study, two N-heterocyclic salts (N,N'-diphenacyl-[4,4'-dipyridinium] dibromide (DP) and N,N'-diphenacyl-1,2-bis-(4-pyridinium)ethane dibromide (DPE)) were used for chitosan functionalization to enhance its antimicrobial potential. Physico-chemical characterization of the newly synthesized derivatives (Ch-DP and Ch-DPE) was performed by elemental analysis, spectrometry (UV-Vis, FTIR), electrochemistry (OCP, CV), and electron microscopy (SEM) proving that the highest degree of functionalization was obtained for Ch-DP. The antimicrobial effect of chitosan functionalization was further tested in terms of its interactio...
Source: Carbohydrate Research - November 5, 2023 Category: Genetics & Stem Cells Authors: Andreea Veronica Dediu Botezatu Roxana-Mihaela Apetrei Iuliana Florina Costea Nour Vasilica Barbu Leontina Grigore-Gurgu Florina Botez Rodica Mihaela Dinica Bianca Furdui Geta C ârâc Source Type: research
Synthesis and characterization of novel chitosan derivatives (containing dipyridinium quaternary salts) with antimicrobial potential
In this study, two N-heterocyclic salts (N,N'-diphenacyl-[4,4'-dipyridinium] dibromide (DP) and N,N'-diphenacyl-1,2-bis-(4-pyridinium)ethane dibromide (DPE)) were used for chitosan functionalization to enhance its antimicrobial potential. Physico-chemical characterization of the newly synthesized derivatives (Ch-DP and Ch-DPE) was performed by elemental analysis, spectrometry (UV-Vis, FTIR), electrochemistry (OCP, CV), and electron microscopy (SEM) proving that the highest degree of functionalization was obtained for Ch-DP. The antimicrobial effect of chitosan functionalization was further tested in terms of its interactio...
Source: Carbohydrate Research - November 5, 2023 Category: Genetics & Stem Cells Authors: Andreea Veronica Dediu Botezatu Roxana-Mihaela Apetrei Iuliana Florina Costea Nour Vasilica Barbu Leontina Grigore-Gurgu Florina Botez Rodica Mihaela Dinica Bianca Furdui Geta C ârâc Source Type: research
Efficient synthesis of glycosylated imidazo[1,2-a]pyridines via solvent catalysed Groebke-Blackburn-Bienayme reaction
Carbohydr Res. 2023 Oct 23;534:108974. doi: 10.1016/j.carres.2023.108974. Online ahead of print.ABSTRACTA solvent catalysed and metal catalyst-free Groebke-Blackburn-Bienayame three component reaction (GBB-3CR) has been developed for the synthesis of 2-(β-D-glycal-1-yl)-3-N-alkylamino-1-azaindolizines and 2-alkyl/aryl/heteroaryl-3-N-alkylamino-1-azaindolizines. The modified GBB reaction protocol is highly efficient, versatile, atom economic and has been performed in hexafluoroisopropanol (HFIP) without any added catalyst. The GBB-3CR showed high tolerance for a large no of substrates in term of aldehydes, differently subs...
Source: Carbohydrate Research - November 3, 2023 Category: Genetics & Stem Cells Authors: Bhawani Shankar Banty Kumar Sumit Kumar Aditi Arora None Kavita Rashmi Tomar Brajendra K Singh Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
N-glycosylation in Archaea: Unusual sugars and unique modifications
Carbohydr Res. 2023 Oct 5;534:108963. doi: 10.1016/j.carres.2023.108963. Online ahead of print.ABSTRACTArchaea are microorganisms that comprise a distinct branch of the universal tree of life and which are best known as extremophiles, residing in a variety of environments characterized by harsh physical conditions. One seemingly universal trait of Archaea is the ability to perform N-glycosylation. At the same time, archaeal N-linked glycans present variety in terms of both composition and architecture not seen in the parallel eukaryal or bacterial processes. In this mini-review, many of the unique and unusual sugars found ...
Source: Carbohydrate Research - October 27, 2023 Category: Genetics & Stem Cells Authors: Anna Notaro Marianna Zaretsky Antonio Molinaro Cristina De Castro Jerry Eichler Source Type: research
Mild method for the synthesis of α-glycosyl chlorides: A convenient protocol for quick one-pot glycosylation
Carbohydr Res. 2023 Oct 20;534:108976. doi: 10.1016/j.carres.2023.108976. Online ahead of print.ABSTRACTA simple and efficient protocol for the preparation of α-glycosyl chlorides within 15-30 min is described which employs a stable, cheap, and commercially available Trichloroisocyanuric acid (TCCA) as non-toxic chlorinating agent along with PPh3. This process involved a wide range of substrate scope and is well-suited with labile hydroxyl protecting groups such as benzyl, acetyl, benzoyl, isopropylidene, benzylidene, and TBDPS (tert-butyldiphenylsilyl) groups. This process is operationally simple, mild conditions and obt...
Source: Carbohydrate Research - October 23, 2023 Category: Genetics & Stem Cells Authors: Ariza Khanam Shashiprabha Dubey Pintu Kumar Mandal Source Type: research
Recent progress in the synthesis of natural product inspired bioactive glycohybrids
Carbohydr Res. 2023 Oct 13;534:108975. doi: 10.1016/j.carres.2023.108975. Online ahead of print.ABSTRACTCarbohydrates are a basic structural component that are indispensable to all cellular processes. In addition to being employed as chiral starting materials in the synthesis of a variety of natural products, carbohydrates are recognized as naturally occurring molecules having an enormous variety of functional, stereochemical, and structural properties. The understanding and biological roles of carbohydrate derived molecules can be greatly improved by selectively synthesizing functional carbohydrates through incorporating ...
Source: Carbohydrate Research - October 23, 2023 Category: Genetics & Stem Cells Authors: Kavita Singh Sunil Sharma Rajdeep Tyagi Ram Sagar Source Type: research
