Suzuki-Miyaura coupling reaction was applied in the syntheses of neoglycopeptides. This work utilizes new type of glycosyl aryl boronic acid and readily accessible iodo amino acids/iodopeptides. Both carbohydrate and peptide moieties are unprotected and the final product could be isolated directly. The neoglyco amino acid and neoglycopeptide products feature an O-glycosyl biaryl linker between the carbohydrate and peptide moieties.
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http://dx.doi.org/10.2174/0929866521666140626103204 | DOI Listing |
Org Lett
December 2024
National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China.
We have developed a glycosyl radical-based synthesis of -alkyl glycosides through a deoxygenative Giese addition-reduction-cyclization cascade, in which readily available 1-hydroxy carbohydrates serve as precursors for glycosyl radicals and aryl alkenes function as radical acceptors. This reaction not only provides an effective method for accessing a previously underexplored class of functionalized cyclopropanes but also enhances the application of Giese addition in the synthesis of -alkyl glycosides by derivatizing the radical intermediate generated through polar cyclization to yield a cyclopropane.
View Article and Find Full Text PDFACS Omega
December 2024
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding, Hebei 071002, P. R. China.
HCl-catalyzed -glycosylation was described herein for the convenient preparation of -heteroaryl -glycosides and polyhydroxylated alkanes with diaryl groups using hetereoaryl amines and unprotected sugars as starting materials. The reaction temperature and the amounts of aryl amines and HCl had significant effects on reactions. The method provided a highly efficient and environmentally friendly route for constructing -glycosides at low cost.
View Article and Find Full Text PDFIUCrdata
October 2024
Department of Chemistry, Kuwait University, PO Box 5969, Safat 13060, Kuwait.
The crystal structure of a glycosyl-ated porphyrin () system, CHNO, where two iso-propyl-idene protected galactose moieties are attached to the position of a substituted tetra-aryl porphyrin is reported. This structure reveals that the parent porphyrin is planar, with the galactose moieties positioned above and below the porphyrin macrocycle. This orientation likely prevents porphyrin-porphyrin H-type aggregation, potentially enhancing its efficiency as a photosensitizer in photodynamic therapy.
View Article and Find Full Text PDFBioorg Med Chem Lett
December 2024
Department of Chemistry, University of Southern California, Los Angeles, CA 90089, USA. Electronic address:
Carbohydrates play crucial roles in biological systems, including by mediating cell and protein interactions. The complexity and transient nature of carbohydrate-dependent interactions pose significant challenges for their characterization, as traditional techniques often fail to capture these low-affinity binding events. This review highlights the increasing utility of photocrosslinkers in studying carbohydrate-mediated interactions.
View Article and Find Full Text PDFCommun Chem
December 2024
Technische Universität Darmstadt, Clemens-Schöpf-Institut für Organische Chemie und Biochemie, Peter-Grünberg-Straße 4, 64287, Darmstadt, Germany.
C-glycosides are significant in medicinal chemistry due to their resistance to enzymatic hydrolysis, making them more stable and bioavailable compared to O-glycosides. Their unique structure also offers potential for developing drugs with improved therapeutic properties, particularly in treating diseases like diabetes and cancer. The main challenge in synthesizing C-glycosides lies in forming the carbon-carbon bond between the sugar and aglycone efficiently, while controlling the stereochemistry and minimizing side reactions.
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