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Stereospecific synthesis of methyl 2-amino-2-deoxy-(6S)-deuterio-α,β-d-glucopyranoside and methyl 2,6-diamino-2,6-dideoxy-(6R)-deuterio-α,β-d-glucopyranoside: Side chain conformations of the 2-amino-2-deoxy and 2,6-diamino-2,6-dideoxyglucopyranosides
| Content Provider | Scilit |
|---|---|
| Author | Kato, Takayuki Vasella, Andrea Crich, David |
| Copyright Year | 2017 |
| Description | Journal: Carbohydrate research The stereospecifically labeled 6-monodeuterio methyl 2,6-diamino-2,6-dideoxy-α- and β- d-glucopyranosides were synthesized with a view to determining their side chain conformations. NMR studies in $D_{2}$O at pH 5 and pH 11 reveal both anomers to adopt very predominantly the gt conformation consistent with the gauche conformation of 2-aminoethanol and its acetate salt. In contrast, as also revealed with the help of stereospecifically-labelled monodeuterio isotopomers, the methyl 2-amino-2-deoxy-α- and β- d-glucopyranosides are an approximately 1:1 mixture of gg and gt conformers as is found in glucopyranose itself. |
| Related Links | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5529286/pdf |
| Ending Page | 17 |
| Page Count | 8 |
| Starting Page | 10 |
| ISSN | 00086215 |
| e-ISSN | 1873426X |
| DOI | 10.1016/j.carres.2017.05.015 |
| Journal | Carbohydrate research |
| Volume Number | 448 |
| Language | English |
| Publisher | Elsevier BV |
| Publisher Date | 2017-05-19 |
| Access Restriction | Open |
| Subject Keyword | Journal: Carbohydrate research Organic Chemistry Side Chain Conformation Deuterium Labelling Conformational Analysis |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Medicine Analytical Chemistry Biochemistry |
