75828-75-0Relevant academic research and scientific papers
Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides
Li, Xiaoqian,Ma, Zhi,Liu, Rongkun,Hurevich, Mattan,Yang, You
supporting information, p. 3309 - 3314 (2021/10/14)
A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. By employing ortho-nitrobenzyl carbonate (oNBC) as PPG, N,N-dimethylformamide (DMF)-modulated SPhosAuNTf2/s
Synthesis of nonnatural nucleoside diphosphate sugars
Wolf, Saskia,Berrio, Rosmirt Molina,Meier, Chris
scheme or table, p. 6304 - 6313 (2011/12/16)
Recently, we reported an efficient chemical method for the synthesis of a variety of naturally occurring nucleoside diphosphate (NDP) sugars. This method, which is based on the cycloSal approach, can also be used, in principle, for the preparation of rare or even nonnatural NDP sugars. Herein, the syntheses of sulfoquinovose-, glucose-6-sulfate-, L-galactose-, and 2-fluoroglycopyranoside- containing NDP sugars are presented, as well as the synthesis of NDP sugars with non-natural nucleosides. The reactions described gavestereoisomerically defined NDP sugars in high yields and short reaction times.
Design and synthesis of functionalized trisaccharides as p53-peptide mimics
Sakurai, Kaori,Kahne, Daniel
scheme or table, p. 3724 - 3727 (2010/08/22)
Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an α-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology.
Synthesis and structure-activity relationship study of isoglobotrihexosylceramide analogues
Chen, Wenlan,Xia, Chengfeng,Wang, Jinhua,Thapa, Prakash,Li, Yusen,Nadas, Janos,Zhang, Wenpeng,Zhou, Dapeng,Wang, Peng George
, p. 9914 - 9923 (2008/09/17)
(Chemical Equation Presented) Invariant natural killer T (iNKT) cells are innate T lymphocytes that express T cell receptors binding to exogenous and endogenous glycosphingolpid antigens presented by a nonpolymorphic, non-MHC antigen presenting molecule,
Efficient Route to 2-Deoxy β-O-Aryl-D-Glycosides via Direct Displacement of Glycosyl Iodides
Lam, Son N.,Gervay-Hague, Jacquelyn
, p. 4219 - 4222 (2007/10/03)
(Equation presented) The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-β-O-aryl
Synthesis of α-galactosyl ceramide, a potent immunostimulatory agent
Plettenburg, Oliver,Bodmer-Narkevitch, Vera,Wong, Chi-Huey
, p. 4559 - 4564 (2007/10/03)
α-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of α-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.
Hydrolytic activity of α-galactosidases against deoxy derivatives of p- nitrophenyl α-D-galactopyranoside
Hakamata, Wataru,Nishio, Toshiyuki,Oku, Tadatake
, p. 107 - 115 (2007/10/03)
The four possible monodeoxy derivatives of p-nitrophenyl (PNP) α-D- galactopyranoside were synthesized, and hydrolytic activities of the α- galactosidase of green coffee bean, Mortierella vinacea and Aspergillus niger against them were elucidated. The 2- and 6-deoxy substrates were hydrolyzed by the enzymes from green coffee bean and M. vinacea, while they scarcely acted on the 3- and 4-deoxy compounds. On the other hand, A. niger α- galactosidase hydrolyzed only the 2-deoxy compound in these deoxy substrates, and the activity was very high. These results indicate that the presence of two hydroxyl groups (OH-3 and -4) is essential for the compounds to act as substrates for the enzymes of green coffee bean and M. vinacea, while the three hydroxyl groups (OH-3, -4, and -6) are necessary for the activity of the A. niger enzyme. The kinetic parameters (K(m) and V(max)) of the enzymes for the hydrolysis of PNP α-D-galactopyranoside and its deoxy derivatives were obtained from kinetic studies. (C) 2000 Elsevier Science Ltd.
Synthetic utility of 1,1,2,2-tetraaryIdisilanes: Radical reduction of alkyl phenyl chalcogenides
Yamazaki, Osamu,Togo, Hidco,Yokoyama, Masataka
, p. 2891 - 2896 (2007/10/03)
Reactivity of tetraaryldisilanes as radical reducing agents of alkyl phenyl chalcogenides initiated by Et3B or AIBN was studied. Here, the reactivity of alkyl sulfide was poor; however, various alkyl phenyl selenides and tellurides were reduced to the corresponding hydrocarbons in good yields with 1,1,2,2-tetraphenyldisilane. The Royal Society of Chemistry 1999.
Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties
Motoki,Morita,Kobayashi,Uchida,Akimoto,Fukushima,Koezuka
, p. 1487 - 1491 (2007/10/03)
Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2- and 4-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.
Efficient synthesis of 2-deoxyglycosyl-1-O-acyl esters via 2-deoxyglycosyl phosphorodithioates as glycosyl donors
Borowiecka,Michalska
, p. 709 - 713 (2007/10/02)
An efficient glycosylation of carboxylic acids 2a-p has been developed employing 2-deoxyglycosyl phosphorodithioates 1a-h as glycosyl donors and Ag + salts as activators. In the case of aliphatic acids the method is highly β-stereoselective. Stereoselecti
