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Keywords = ribono-1,4-lactone

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12 pages, 6576 KiB  
Article
Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones
by Abed Bil, Bemba Abdellahi, Gwladys Pourceau and Anne Wadouachi
Sustain. Chem. 2022, 3(3), 300-311; https://doi.org/10.3390/suschem3030019 - 22 Jun 2022
Cited by 6 | Viewed by 2933
Abstract
Sugar amides, such as aldonamides, are interesting, sugar-based molecules used in various fields, from detergency to medicine. Nevertheless, their valorization, especially as alternatives to petroleum-based substances, can be slowed down by their synthetic pathway, which is generally not in accordance with green chemistry [...] Read more.
Sugar amides, such as aldonamides, are interesting, sugar-based molecules used in various fields, from detergency to medicine. Nevertheless, their valorization, especially as alternatives to petroleum-based substances, can be slowed down by their synthetic pathway, which is generally not in accordance with green chemistry principles, and is also not economically competitive. We propose herein a fast procedure for the synthesis of aldonamide-derived glycoconjugates with mechanochemistry. The conditions were first optimized with galactonolactone, used as a model lactone, and dodecylamine. After only 5 min of grinding of stoechiometric amounts of amine and lactone, in the presence of water used as a Liquid Assisted Grinding (LAG) agent, the corresponding galactonamide was isolated with a high yield (90%) after a simple aqueous work-up. The optimized conditions were then applied to a wide variety of amines and sugar lactones, showing the versatility of the methodology. Gluco- and ribono-lactone exhibited similarly excellent reactivity, showing that the procedure is not sugar-dependent. Furthermore, the procedure was shown to be compatible with various functional groups such as alkene, alkyne, thiol, ester and hydroxyl. Full article
(This article belongs to the Topic Green and Sustainable Chemistry)
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16 pages, 1528 KiB  
Article
Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of C-Nucleosides
by Silvana Casati, Paola Rota, Pietro Allevi, Alessandra Mingione, Roberta Ottria and Pierangela Ciuffreda
Molecules 2021, 26(21), 6447; https://doi.org/10.3390/molecules26216447 - 26 Oct 2021
Cited by 3 | Viewed by 2617
Abstract
In the last two years, nucleosides analogues, a class of well-established bioactive compounds, have been the subject of renewed interest from the scientific community thanks to their antiviral activity. The COVID-19 global pandemic, indeed, spread light on the antiviral drug Remdesivir, an adenine [...] Read more.
In the last two years, nucleosides analogues, a class of well-established bioactive compounds, have been the subject of renewed interest from the scientific community thanks to their antiviral activity. The COVID-19 global pandemic, indeed, spread light on the antiviral drug Remdesivir, an adenine C-nucleoside analogue. This new attention of the medical community on Remdesivir prompts the medicinal chemists to investigate once again C-nucleosides. One of the essential building blocks to synthetize these compounds is the D-(+)-ribono-1,4-lactone, but some mechanistic aspects linked to the use of different carbohydrate protecting groups remain unclear. Here, we present our investigations on the use of benzylidene as a ribonolactone protecting group useful in the synthesis of C-purine nucleosides analogues. A detailed 1D and 2D NMR structural study of the obtained compounds under different reaction conditions is presented. In addition, a molecular modeling study at the B3LYP/6-31G* level of theory with the SM8 solvation model for CHCl3 and DMSO to support the obtained results is used. This study allows for clarifying mechanistic aspects as the side reactions and structural rearrangements liked to the use of the benzylidene protecting group. Full article
(This article belongs to the Special Issue Synthesis, Quantification and NMR Characterization of Bioactive Compounds)
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11 pages, 2207 KiB  
Article
New Methyl Threonolactones and Pyroglutamates of Spilanthes acmella (L.) L. and Their Bone Formation Activities
by Retno Widyowati, Melanny Ika Sulistyowaty, Nguyen Hoang Uyen, Sachiko Sugimoto, Yoshi Yamano, Hideaki Otsuka and Katsuyoshi Matsunami
Molecules 2020, 25(11), 2500; https://doi.org/10.3390/molecules25112500 - 28 May 2020
Cited by 5 | Viewed by 3209
Abstract
In our continuing research for bioactive constituents from natural resources, a new methyl threonolactone glucopyranoside (1), a new methyl threonolactone fructofuranoside (2), 2 new pyroglutamates (3 and 4), and 10 known compounds (5–14) [...] Read more.
In our continuing research for bioactive constituents from natural resources, a new methyl threonolactone glucopyranoside (1), a new methyl threonolactone fructofuranoside (2), 2 new pyroglutamates (3 and 4), and 10 known compounds (5–14) were isolated from the whole plant of Spilanthes acmella (L.) L. The structures of these compounds were determined based on various spectroscopic and chemical analyses. All of the isolated compounds were evaluated on bone formation parameters, such as ALP (alkaline phosphatase) and mineralization stimulatory activities of MC3T3-E1 cell lines. The results showed that the new compound, 1,3-butanediol 3-pyroglutamate (4), 2-deoxy-d-ribono-1,4-lactone (6), methyl pyroglutamate (7), ampelopsisionoside (10), icariside B1 (11), and benzyl α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside (12) stimulated both ALP and mineralization activities. Full article
(This article belongs to the Special Issue Plant Natural Products: Isolation, Identification and Biological Activity)
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8 pages, 973 KiB  
Communication
Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone
by Michael R. Imrich and Thomas Ziegler
Molbank 2019, 2019(4), M1096; https://doi.org/10.3390/M1096 - 10 Dec 2019
Cited by 1 | Viewed by 3875
Abstract
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l [...] Read more.
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l-psicose derivative as an anomeric mixture in 72% yield. Both methylated psicoses were further converted into 1,2-O-isopropylidene-3,4,6-tri-O-methyl-d- and l-psicofuranosides, the respective α- and β-anomers of which could be separated and characterized. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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