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Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

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  • معلومة اضافية
    • Contributors:
      Institut Parisien de Chimie Moléculaire (IPCM); Chimie Moléculaire de Paris Centre (FR 2769); École normale supérieure - Paris (ENS-PSL); Université Paris Sciences et Lettres (PSL)-Université Paris Sciences et Lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP); Université Paris Sciences et Lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris); Université Paris Sciences et Lettres (PSL)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL); Université Paris Sciences et Lettres (PSL)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS); Università degli Studi di Pavia = University of Pavia (UNIPV); University of Canterbury Christchurch
    • بيانات النشر:
      HAL CCSD
      Wiley-VCH Verlag
    • الموضوع:
      2019
    • Collection:
      ESPCI ParisTech: HAL (Ecole Supérieure de Physique et Chimie Industrielles)
    • نبذة مختصرة :
      International audience ; Highly regioselective deprotection of a series of 2‐amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo‐glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo‐glycoproteins with an N‐acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.
    • Relation:
      hal-02180805; https://hal.sorbonne-universite.fr/hal-02180805; https://hal.sorbonne-universite.fr/hal-02180805/document; https://hal.sorbonne-universite.fr/hal-02180805/file/manuscript20190416_sans%20marque.pdf
    • الرقم المعرف:
      10.1002/ejoc.201900382
    • الدخول الالكتروني :
      https://hal.sorbonne-universite.fr/hal-02180805
      https://hal.sorbonne-universite.fr/hal-02180805/document
      https://hal.sorbonne-universite.fr/hal-02180805/file/manuscript20190416_sans%20marque.pdf
      https://doi.org/10.1002/ejoc.201900382
    • Rights:
      info:eu-repo/semantics/OpenAccess
    • الرقم المعرف:
      edsbas.87FC4C5E