10343-15-4Relevant articles and documents
Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols
Narayanaperumal, Senthil,Da Silva, Rodrigo Ce?sar,Monteiro, Julia L.,Corre?a, Arlene G.,Paixa?o, Ma?rcio W.
, p. 1982 - 1988 (2012)
In this work, the use of ferric chloride as an efficient catalyst in glycosylation reactions of sugars in the presence of allyl and alkynyl alcohols is described. The corresponding glycosides were obtained with moderate to good yields. This new procedure presented greater selectivity when compared to classic methods found in the literature. Principal features of this simple method include non-hazardous reaction conditions, low-catalyst loading, good yields and high anomeric selectivity.
Synthesis of the allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America
Olsen, Carl Erik,M?ller, Birger Lindberg,Motawia, Mohammed Saddik
, p. 13 - 16 (2014)
The allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America, was chemically synthesized using an efficient and practical synthetic strategy based on a simple reaction sequence. Commercially available 1,2,3,4,6-penta-O-acetyl- β-d-glucopyranose was converted into prop-2-enyl 2,3,4,6-tetra-O-acetyl- β-d-glucopyranoside and subjected to epoxidation. In a one-pot reaction, ring-opening of the epoxide using TMSCN under solvent free conditions followed by treatment of the formed trimethylsilyloxy nitrile with pyridine and phosphoryl chloride, afforded the acetylated β-unsaturated nitriles (Z)-4-(2,3,4,6-tetra-O-β-d-glucopyranosyloxy)but-2-enenitrile and its isomer (E)-4-(23,4,6-tetra-O-β-d-glucopyranosyloxy)but-2-enenitrile. Deacetylation of Z- and/or E-isomers afforded the target molecules alliarinoside and its isomer.
Mannose/glucose-functionalized dendrimers to investigate the predictable tunability of multivalent interactions
Wolfenden, Mark L.,Cloninger, Mary J.
, p. 12168 - 12169 (2005)
G4-, G5-, and G6-PAMAM dendrimers were functionalized with mixtures of mannose and glucose in varying ratios, and the relative affinities of these compounds for Concanavalin A (Con A) were evaluated using the hemagglutination assay. As the ratio of mannose to glucose increases, the relative activity in the hemagglutination assay (on a per sugar basis) increases linearly. Methyl mannose binds to Con A with an affinity 4-fold higher than that of methyl glucose; multivalency amplifies this trend. The mannose/glucose-functionalized dendrimer results reported here suggest that the affinity of multivalent associations can be attenuated in predictable, reliable ways based on monovalent affinities of the ligands. Copyright
A cyanoallyl glucoside from Alliaria petiolata, as a feeding deterrent for larvae of Pieris napi oleracea
Haribal, Meena,Yang, Zhicai,Attygalle, Athula B.,Renwick, J. Alan A.,Meinwald, Jerrold
, p. 440 - 443 (2001)
Alliarinoside, a feeding inhibitor against early instar larvae of Pieris napi oleracea, was isolated from the foliage of Alliaria petiolata and characterized as (2Z)-4-(β-D-glucopyranosyloxy)-2-butenenitrile (1) by spectroscopic methods. The structural assignment was confirmed by synthesis of peracetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. Feeding inhibition assays showed comparable activity for the synthetic and natural glycosides.
A new type of carbohydrate-containing synthetic antigen: synthesis of carbohydrate-containing polysaccharide copolymers with the specifity of O:3 and O:4 factors of Salmonella
Kochetkov, Nikolay K.,Dmitriev, Boris A.,Chernyak, Anatoli Ya.,Levinsky, Anatoli B.
, p. C16 - C20 (1982)
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Photoinduced Thiol-ene Chemistry Applied to the Synthesis of Self-Assembling Elastin-Inspired Glycopeptides
Piccirillo, Germano,Pepe, Antonietta,Bedini, Emiliano,Bochicchio, Brigida
, p. 2648 - 2659 (2017)
Synthetic (glyco)peptides inspired by proteins able to self-assemble are appealing biomaterials in the field of tissue engineering and regenerative medicine. Herein, for the first time, taking advantage of thiol-ene chemistry coupled to solid-phase peptide synthesis, a self-assembling peptide inspired by elastin protein was bioconjugated to three carbohydrates in order to obtain the corresponding glycopeptides. They were studied at the molecular and supramolecular level. The results show that the carbohydrate influences the molecular conformation of the glycopeptide and its self-aggregation properties as well. As future perspective, the results could enable us to tune the final self-aggregation properties of the glycopeptide by changing the sugar moiety.
A synthesis of diastereomeric isofloridoside
Beier, Ross C.,Mundy, Bradford P.,Strobel, Gary A.
, p. 141 - 143 (1981)
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A high-yielding synthesis of allyl glycosides from peracetylated glycosyl donors
Khamsi, Jamal,Ashmus, Roger A.,Schocker, Nathaniel S.,Michael, Katja
, p. 147 - 150 (2012)
β-Configured peracetylated sugars are often used as easily accessible glycosyl donors that are typically activated with common Lewis acids such as boron trifluoride or trimethylsilyltrifluoromethane sulfonate. Often these glycosylations occur with unsatisfactory yields due to incomplete reactions or extensive byproduct formation, primarily as a result of loss of an additional acetyl group generating partially unprotected glycosides. Here we report a simple glycosylation-reacetylation protocol for the generation of predominantly β-configured peracetylated allyl glucoside, -galactoside, -lactoside, and -maltoside with substantially improved reaction yields.
Synthesis of β-galactose-conjugated chlorins derived by enyne metathesis as galectin-specific photosensitizers for photodynamic therapy
Zheng,Graham,Shibata,Missert,Oseroff,Dougherty,Pandey
, p. 8709 - 8716 (2001)
A first report on the synthesis and biological evaluation of the β-galactose-conjugated purpurinimides (a class of chlorins containing a six-membered fused imide ring system) as Gal-1 (galectin-1) recognized photosensitizers, prepared from purpurin-N-propargylimide via enyne metathesis, is discussed. On the basis of examination of the available crystal structure of the galectin-1 N-acetyllactose amine complex, it was considered that the chlorin-based photosensitizers could be introduced into a carbohydrate skeleton to expand the repertoire of the galectin-1-specific ligands. Preliminary molecular modeling analysis utilizing the modeled photosensitizers and the available crystal structures of galectin-carbohydrate complexes indicated that addition of the photosensitizer to the carbohydrate moiety at an appropriate position does not interfere with the galectin-carbohydrate recognition. Under similar drug and light doses, compared to the free purpurinimide analogue, the purpurinimides conjugated either with galactose or with lactose (Gal(β1-4)-Glc) produced a considerable increase in photosensitizing efficacy in vitro. This indicates the possibility for development of a new class of specific photosensitizers for photodynamic therapy (PDT) based on recognition of a cellular receptor.
Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
Bernardes, Gon?alo J. L.,Day, Jason,Domingos, Josiel B.,Jiménez-Moreno, Ester,Kon?, Juraj,Latocheski, Eloah,Pérez, Laura Rodríguez,Sabatino, Valerio
supporting information, (2022/01/11)
Owing to their bioorthogonality, transition metals have become very popular in the development of biocompatible bond-cleavage reactions. However, many approaches require design and synthesis of complex ligands or formulation of nanoparticles which often perform poorly in living cells. This work reports on a method for the generation of an active palladium species that triggers bond-cleaving reactions inside living cells. We utilized the water-soluble Na2PdCl4 as a simple source of PdII which can be intracellularly reduced by sodium ascorbate to the active Pd0 species. Once generated, Pd0 triggers the cleavage of allyl ether and carbamate caging groups leading to the release of biologically active molecules. These findings do not only expand the toolbox of available bioorthogonal dissociative reactions but also provide an additional strategy for controlling the reactivity of Pd species involved in Pd-mediated bioorthogonal reactions.
Acid-Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water
Timmer, Brian J. J.,Ramstr?m, Olof
supporting information, p. 14408 - 14413 (2019/11/11)
The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda–Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized α-d-manno- and α-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis with allyl alcohol could also be achieved with reasonable selectivity. The presence of small quantities (2.5 vol %) of acetic acid increased the formation of the self-metathesis product while significantly reducing the alkene isomerization process. The catalytic activity was furthermore retained in the presence of large amounts (0.01 mm) of protein, underlining the potential of this carbon–carbon bond-forming reaction under biological conditions. These results demonstrate the potential of directly using unprotected carbohydrate structures in olefin metathesis reactions under mild conditions compatible with biological systems, and thereby enabling their use in, for example, drug discovery and protein derivatization.
