205676-46-6Relevant academic research and scientific papers
Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks
Anjum, Shazia,Vetter, Natasha D.,Rubin, Joseph E.,Palmer, David R.J.
supporting information, p. 816 - 825 (2013/07/25)
Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1′-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene- α-δ-glucofuranose. The key a,b-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1′-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity.
Glycodiversification for the optimization of the kanamycin class aminoglycosides
Wang, Jinhua,Li, Jie,Chen, Hsiao-Nung,Chang, Huiwen,Tanifum, Christabel Tomla,Liu, Hsiu-Hsiang,Czyryca, Przemyslaw G.,Chang, Cheng-Wei Tom
, p. 6271 - 6285 (2007/10/03)
In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The a
Glycosylation of cyclitols: Synthesis of neamine-type aminoglycosides
Verhelst, Steven H. L.,Magnee, Lisette,Wennekes, Tom,Wiedenhof, Wouter,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Van Boeckel, Constant A. A.,Van Boom, Jacques H.
, p. 2404 - 2410 (2007/10/03)
In this paper, a glycosylation-based approach towards novel aminoglycoside analogues is presented. Three different cyclitol building blocks were condensed with different thioglycosides to give, after removal of the protective groups, several neamine-type
Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: Correlation of antibiotic activity with in vitro inhibition of translation
Greenberg, William A.,Priestley, E. Scott,Sears, Pamela S.,Alper, Phil B.,Rosenbohm, Christoph,Hendrix, Martin,Hung, Shang-Cheng,Wong, Chi-Huey
, p. 6527 - 6541 (2007/10/03)
The structure and activity of the pseudodisaccharide core found in aminoglycoside antibiotics was probed with a series of synthetic analogues in which the position of amino groups was varied around the glucopyranose ring. The naturally occurring structure
Total synthesis of (-)-hikizimycin employing the strategy of two-directional chain synthesis
Ikemoto, Norihiro,Schreiber, Stuart L.
, p. 2524 - 2536 (2007/10/02)
Hikizimycin (anthelmycin) is a nucleoside antibiotic and anthelmintic agent that represents the most structurally complex member of the long-chain carbohydrate class of natural products. The undecose moiety of hikizimycin was constructed efficiently by em
