3068-31-3Relevant academic research and scientific papers
"Click" glycodendrimers containing 27, 81, and 243 modified xylopyranoside termini
Camponovo, Jeremy,Hadad, Caroline,Ruiz, Jaime,Cloutet, Eric,Gatard, Sylvain,Muzart, Jacques,Bouquillon, Sandrine,Astruc, Didier
, p. 5071 - 5074 (2009)
(Chemical Equation Presented) A series of large glycodendrimers containing 27, 81, and 243 terminal modified xylose branches from the first (G 1-27) to the third generation (G3-243) were synthesized from 2′-azidoethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside and alkynyl-terminated dendrimers by "click" chemistry that is confirmed to be an excellent method to obtain large glycodendrimers exemplified by the use of modified xylose. The dendrimers were first characterized by 1H NMR, 13C{1H} NMR, elemental analysis, and IR spectroscopy. The size progression in the series was also demonstrated using both DOSY NMR and size exclusion chromatography (SEC), the latter technique showing the good polydispersity of all the dendrimers. The size measured by dynamic light scattering (DLS) for the dendrimer G3-243 is close to that obtained by the DOSY NMR method.
Tandem β-elimination-Morita-Baylis-Hillman reaction in α,β-unsaturated sugar aldehydes
Areces, Pilar,Carrasco, Esther,Mancha, Alicia,Plumet, Joaquin
, p. 946 - 948 (2006)
The first Morita-Baylis-Hillman reaction of a 1-formylbutadiene derivative is reported. In addition, a convenient synthesis of 2-acetoxy-4-formylbutadiene derivatives starting from easily available D-galactal and D-arabinal is also described. Georg Thieme Verlag Stuttgart.
Chemical synthesis and in vitro antitumor activity of quinizarin glycoside analogs
Sun, Xiaofei,Ji, Li,Ren, Sumei,Wan, Shengbiao,Jiang, Tao
, p. 4116 - 4124 (2008)
A series of new glycoside derivatives of quinizarin were synthesized and characterized by NMR and IR spectrometry, and in vitro antitumor activity of some of these derivatives was evaluated against the mouse leukaemia P388 and the human leukaemia HL-60 cell lines by the standard MTT assay. They were proven to possess moderate antitumor activity. Copyright Taylor & Francis Group, LLC.
Photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals towards the stereoselective synthesis of α-1-fluoroalkyl-: C -glycosyl derivatives
Mora Flores, Erwin W.,Postigo, Al,Uhrig, María Laura
, p. 8724 - 8734 (2020)
A benign, efficient, regio- and stereoselective protocol for the syntheses of α-1-fluoroalkyl-C-glycosyl compounds bearing CF3, C4F9, and C6F13 substituents on the anomeric carbon has been developed by a new methodology starting from 2-acetoxyglycals for the first time. Remarkably, the reactions proceeded in only one step, through the visible light-photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals by means of an Ir photocatalyst and employed commercially available fluoroalkyl iodides n-CnF2n+1-I (n = 1, 4, 6) as a source of fluoroalkyl radicals.
Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates
Liu, Peng,Mukherjee, Upasana,Ngai, Ming-Yu,Wu, Yue,Yao, Wang,Zhao, Gaoyuan,Zhou, Lin
supporting information, p. 3353 - 3359 (2022/03/08)
Excited-state palladium catalysis has emerged as a promising strategy for developing novel and valuable reactions. Herein, we report the first excited-state Pd-catalyzed 1,2-radical migratory Mizoroki-Heck reaction that enables C2-alkenylation of carbohydrates using readily available 1-bromosugars and alkenes. The reaction tolerates a wide variety of functional groups and complex molecular architectures, including derivatives of natural products and marketed drugs. Preliminary mechanistic studies and DFT calculations suggest the involvement of visible-light-induced photoexcitation of Pd species, 1,2-spin-centered-shift (SCS) process, and Heck-type cross-coupling reaction. The reaction expands the reactivity profile of excited-state Pd catalysis and provides a streamlined protocol for the preparation of a wide variety of C2-alkenylated carbohydrate mimetics to aid the discovery and development of new therapeutics, agrochemicals, and materials.
Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates
Zhao, Gaoyuan,Yao, Wang,Mauro, Jaclyn N.,Ngai, Ming-Yu
supporting information, p. 1728 - 1734 (2021/02/06)
Excited-state catalysis, a process that involves one or more excited catalytic species, has emerged as a powerful tool in organic synthesis because it allows access to the excited-state reaction landscape for the discovery of novel chemical reactivity. Herein, we report the first excited-state palladium-catalyzed 1,2-spin-center shift reaction that enables site-selective functionalization of carbohydrates. The strategy features mild reaction conditions with high levels of regio- and stereoselectivity that tolerate a wide range of functional groups and complex molecular architectures. Mechanistic studies suggest a radical mechanism involving the formation of hybrid palladium species that undergoes a 1,2-spin-center shift followed by the reduction, deuteration, and iodination to afford functionalized 2-deoxy sugars. The new reactivity will provide a general approach for the rapid generation of natural and unnatural carbohydrates.
Neuroprotective activity of different monosaccharide-modified gastrodin analogs
Xu, Kun-Lun,Yu, Lan
, p. 1263 - 1269 (2020/01/21)
Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.
Chemical synthesis of 5’-β-glycoconjugates of vitamin B6
Bachmann, Thomas,Schnurr, Christian,Zainer, Laura,Rychlik, Michael
supporting information, (2020/02/15)
Various 5’-β-saccharides of pyridoxine, namely the mannoside, galactoside, arabinoside, maltoside, cellobioside and glucuronide, were synthesized chemically according to KOENIGS-KNORR conditions using α4,3-O-isopropylidene pyridoxine and the respective acetobromo glycosyl donors with AgOTf (3.0 eq.) and NIS (3.0 eq.) as promoters at 0 °C. Furthermore, 5’-β-[13C6]-labeled pyridoxine glucoside (PNG) was prepared starting from [13C6]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5’-β-pyridoxal glucoside (PLG).
Folding control of a non-natural glycopeptide using saccharide-coded structural information for polypeptides
Fujii, Naoka,Haino, Takeharu,Ishido, Yuki,Kanbayashi, Naoya,Okamura, Taka-Aki,Onitsuka, Kiyotaka
supporting information, p. 2767 - 2770 (2020/03/13)
We synthesized "glyco-arylopeptides", whose folding structure significantly changes depending on the kind of saccharide in their side chain. The saccharide moiety interacts with the main chain via hydrogen bonding, and the non-natural polypeptides form two well-defined architectures - (P)-31- and (M)-41-helices - depending on the length of the saccharide chains and even the configuration of a single stereo-genic center in the epimers.
On the Catalytic Activity of a GT1 Family Glycosyltransferase from Streptomyces venezuelae ISP5230
Forget, Stephanie M.,Shepard, Sydney B.,Soleimani, Ebrahim,Jakeman, David L.
, p. 11482 - 11492 (2019/10/02)
GT1 family glycosyltansferase, Sv0189, from Streptomyces venezuelae ISP5230 (ATCC 10721) was characterized. The recombinantly produced protein Sv0189 possessed UDP-glycosyltransferase activity. Screening, using an assay employing unnatural nitrophenyl glycosides as activated donors, resulted in the discovery of a broad substrate scope with respect to both acceptor molecules and donor sugars. In addition to polyphenols, including anthraquinones, simple aromatics containing primary or secondary alcohols, a variety of complex natural products and synthetic drugs were glucosylated or xylosylated by Sv0189. Regioselectivity was established through the isolation and characterization of glucosylated products. Sv0189 and homologous proteins are widely distributed among Streptomyces species, and their apparent substrate promiscuity reveals potential for their development as biocatalysts for glycodiversification.
