Synthesis of cyclic α-1,4-oligo--acetylglucosamine 'cyclokasaodorin' a one-pot electrochemical polyglycosylation-isomerization-cyclization process
Electrochemical synthesis of unnatural cyclic oligosaccharides composed of N -acetylglucosamine with α-1,4-glycosidic linkages has been accomplished. A thioglycoside monomer equipped with the 2,3-oxazolidinone protecting group was used to prepare linear oligosaccharides by electrochemical polyglycos...
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| Published in | Chemical communications (Cambridge, England) Vol. 58; no. 57; pp. 7948 - 7951 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Published |
14.07.2022
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| Online Access | Get full text |
| ISSN | 1359-7345 1364-548X |
| DOI | 10.1039/d2cc02287g |
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| Abstract | Electrochemical synthesis of unnatural cyclic oligosaccharides composed of
N
-acetylglucosamine with α-1,4-glycosidic linkages has been accomplished. A thioglycoside monomer equipped with the 2,3-oxazolidinone protecting group was used to prepare linear oligosaccharides by electrochemical polyglycosylation. In the same pot, isomerization of the linear oligosaccharides and intramolecular electrochemical glycosylation for cyclization were also conducted sequentially to obtain the precursor of the cyclic α-1,4-oligo-
N
-acetylglucosamine 'cyclokasaodorin'.
The first synthesis of the
N
-acetylglucosamine analogue of α-cyclodextrin has been achieved using the one-pot electrochemical polyglycosylation-isomerization-cyclization process as a key step. |
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| AbstractList | Electrochemical synthesis of unnatural cyclic oligosaccharides composed of
N
-acetylglucosamine with α-1,4-glycosidic linkages has been accomplished. A thioglycoside monomer equipped with the 2,3-oxazolidinone protecting group was used to prepare linear oligosaccharides by electrochemical polyglycosylation. In the same pot, isomerization of the linear oligosaccharides and intramolecular electrochemical glycosylation for cyclization were also conducted sequentially to obtain the precursor of the cyclic α-1,4-oligo-
N
-acetylglucosamine 'cyclokasaodorin'.
The first synthesis of the
N
-acetylglucosamine analogue of α-cyclodextrin has been achieved using the one-pot electrochemical polyglycosylation-isomerization-cyclization process as a key step. |
| Author | Hamada, Tomoaki Kawano, Takahiro Rahman, Md Azadur Endo, Hirofumi Ochi, Masaharu Nokami, Toshiki |
| AuthorAffiliation | Koganei Corporation Faculty of Engineering Tottori University Department of Chemistry and Biotechnology Centre for Research on Green Sustainable Chemistry |
| AuthorAffiliation_xml | – name: Koganei Corporation – name: Centre for Research on Green Sustainable Chemistry – name: Faculty of Engineering – name: Tottori University – name: Department of Chemistry and Biotechnology |
| Author_xml | – sequence: 1 givenname: Hirofumi surname: Endo fullname: Endo, Hirofumi – sequence: 2 givenname: Masaharu surname: Ochi fullname: Ochi, Masaharu – sequence: 3 givenname: Md Azadur surname: Rahman fullname: Rahman, Md Azadur – sequence: 4 givenname: Tomoaki surname: Hamada fullname: Hamada, Tomoaki – sequence: 5 givenname: Takahiro surname: Kawano fullname: Kawano, Takahiro – sequence: 6 givenname: Toshiki surname: Nokami fullname: Nokami, Toshiki |
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| ContentType | Journal Article |
| DOI | 10.1039/d2cc02287g |
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| Notes | https://doi.org/10.1039/d2cc02287g Electronic supplementary information (ESI) available: Experimental procedures and spectral data of new compounds. See DOI |
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| Snippet | Electrochemical synthesis of unnatural cyclic oligosaccharides composed of
N
-acetylglucosamine with α-1,4-glycosidic linkages has been accomplished. A... |
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| StartPage | 7948 |
| Title | Synthesis of cyclic α-1,4-oligo--acetylglucosamine 'cyclokasaodorin' a one-pot electrochemical polyglycosylation-isomerization-cyclization process |
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