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An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin.
Chem Sci
February 2021
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, University of Chinese Academy of Sciences, Chinese Academy of Sciences Kunming 650201 China
Both glycans (-glycosides) and nucleosides (-glycosides) play important roles in numerous biological processes. Chemical synthesis is a reliable and effective means to solve the attainability issues of these essential biomolecules. However, due to the stereo- and regiochemical issues during glycan assembly, together with problems including the poor solubility and nucleophilicity of nucleobases in nucleoside synthesis, the development of one-pot glycosylation strategies toward efficient synthesis of both glycans and nucleosides remains poor and challenging.
View Article and Find Full Text PDFEfficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf.
Carbohydr Res
June 2012
Department of Chemistry, Jadavpur University, Kolkata 700 032, India.
N-(p-Methylphenylthio)-ε-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy.
View Article and Find Full Text PDFAcyl and silyl group effects in reactivity-based one-pot glycosylation: synthesis of embryonic stem cell surface carbohydrates Lc4 and IV(2)Fuc-Lc4.
J Am Chem Soc
March 2012
Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei 115, Taiwan.
Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.
View Article and Find Full Text PDFSwitching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide.
Org Biomol Chem
March 2012
WestCHEM, School of Chemistry, University of Glasgow, Glasgow, United Kingdom.
5-(2-bromoethyl)phenanthridinium bromide (BEP) undergoes a 3-step-one-pot cyclisation reaction with primary amines allowing the facile synthesis of a vast library of heterocycles. A diverse range of primary aryl amines were explored as reactants to gain insight into the product isolated as a result of the steric and electronic effects of the aryl precursors. Analysis and reaction monitoring with UV-vis and NMR spectroscopy revealed that excessively electron withdrawing groups and sterically hindered amines do not allow for isolation of the common neutral tetrahydroimidazophenanthridine (TIP) structure but allow either the isolation of the charged dihydroimadazophenanthridinium (DIP) or aminoethylphenanthridinium (AEP) products.
View Article and Find Full Text PDFProgrammable one-pot glycosylation.
Top Curr Chem
July 2011
Genomics Research Center, Academia Sinica, Nankang, Taipei 115, Taiwan.
In oligosaccharide synthesis, protecting groups, possible participating groups, promoters/catalysts, reaction conditions, and donor leaving groups and acceptors must all be carefully designed in order to generate the correct regio- and stereochemistry for the new glycosidic bond. Programmable one-pot synthesis has been developed to address the above problems. This strategy is based on the sequential use of thioglycoside building blocks to form glycosidic bonds based on the reactivity difference of the building blocks.
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