N-Acetylmuramyl-L-alanyl-D-isoglutamine α-phenylglycoside was synthesized from α-phenyl-D-glucosaminide peracetate, which was obtained by fusing β-D-glucosamine pentaacetate with phenol and zinc chloride followed by deacetylation. α-Phenyl-N-acetylglucosaminide was converted in two steps into 4,6-O-isopropylidene-N-acetyl-D-muramic acid α-phenylglycoside, which was condensed with L-Ala-D-iGln benzyl ether using the activated ester method. Sequential removal of glycopeptide protecting groups via acid hydrolysis and catalytic hydrogenolysis gave the target product.
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Acknowledgment
The work was performed using equipment (Thermo Scientific MS/MS TSQ Quantum Access MAX) obtained through the Development Program of V. I. Vernadsky Crimean Federal University for 2015-2024.
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2020, pp. 173–176.
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Zemlyakov, A.E., Tsikalova, V.N. & Tsikalov, V.V. Synthesis of N-Acetylmuramyl-L-Alanyld- Isoglutamine α-Phenylglycoside. Chem Nat Compd 56, 193–196 (2020). https://doi.org/10.1007/s10600-020-02986-4
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DOI: https://doi.org/10.1007/s10600-020-02986-4