Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides
The synthesis of monosaccharide units functionalised with different amino acids is described herein. Sugar amino acid templates linked at position 6 of the sugar were prepared by various nucleophilic substitutions introducing a spacer of variable length or by traceless Staudinger ligation....
| Main Authors: | , , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
2007-05-01
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| Series: | CHIMIA |
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| Online Access: | https://chimia.ch/chimia/article/view/4329 |
| _version_ | 1811320053737455616 |
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| author | Christelle Jablonski-Lorin Matthias Nold Arthur Bodenmüller Ernst Hungerbühler |
| author_facet | Christelle Jablonski-Lorin Matthias Nold Arthur Bodenmüller Ernst Hungerbühler |
| author_sort | Christelle Jablonski-Lorin |
| collection | DOAJ |
| description |
The synthesis of monosaccharide units functionalised with different amino acids is described herein. Sugar amino acid templates linked at position 6 of the sugar were prepared by various nucleophilic substitutions introducing a spacer of variable length or by traceless Staudinger ligation.
Sugar amino acid templates attached at the anomeric position and representing a class of precursors of glycopeptides were synthesized in three steps via addition of a solution of trimethylsilylnitrate-trimethylsilylazide on a glycal, followed by subsequent reduction of the sugar azide
and coupling with diverse amino acids.
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| first_indexed | 2024-04-13T12:52:43Z |
| format | Article |
| id | doaj.art-233ccc357a444cb79adc6d4c3f721c0e |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-04-13T12:52:43Z |
| publishDate | 2007-05-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-233ccc357a444cb79adc6d4c3f721c0e2022-12-22T02:46:08ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242007-05-0161510.2533/chimia.2006.286Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of GlycopeptidesChristelle Jablonski-LorinMatthias NoldArthur BodenmüllerErnst Hungerbühler The synthesis of monosaccharide units functionalised with different amino acids is described herein. Sugar amino acid templates linked at position 6 of the sugar were prepared by various nucleophilic substitutions introducing a spacer of variable length or by traceless Staudinger ligation. Sugar amino acid templates attached at the anomeric position and representing a class of precursors of glycopeptides were synthesized in three steps via addition of a solution of trimethylsilylnitrate-trimethylsilylazide on a glycal, followed by subsequent reduction of the sugar azide and coupling with diverse amino acids. https://chimia.ch/chimia/article/view/4329GlycopeptidesStaudinger ligationSugar amino acid templatesSugar azide |
| spellingShingle | Christelle Jablonski-Lorin Matthias Nold Arthur Bodenmüller Ernst Hungerbühler Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides CHIMIA Glycopeptides Staudinger ligation Sugar amino acid templates Sugar azide |
| title | Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides |
| title_full | Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides |
| title_fullStr | Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides |
| title_full_unstemmed | Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides |
| title_short | Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides |
| title_sort | versatile approaches to sugar amino acid building blocks as precursors of glycopeptides |
| topic | Glycopeptides Staudinger ligation Sugar amino acid templates Sugar azide |
| url | https://chimia.ch/chimia/article/view/4329 |
| work_keys_str_mv | AT christellejablonskilorin versatileapproachestosugaraminoacidbuildingblocksasprecursorsofglycopeptides AT matthiasnold versatileapproachestosugaraminoacidbuildingblocksasprecursorsofglycopeptides AT arthurbodenmuller versatileapproachestosugaraminoacidbuildingblocksasprecursorsofglycopeptides AT ernsthungerbuhler versatileapproachestosugaraminoacidbuildingblocksasprecursorsofglycopeptides |