Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone
| Autor: | Romina V. Gómez, Adriana A. Kolender, Oscar Varela |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Alanine
chemistry.chemical_classification Stereochemistry Organic Chemistry Diastereomer Sugar Acids Amino Sugars Stereoisomerism General Medicine Heptoses Biochemistry Analytical Chemistry Amino acid Hydrolysis chemistry.chemical_compound chemistry Hydrogenolysis Carbohydrate Conformation Azide Derivative (chemistry) Lactone |
| Zdroj: | Carbohydrate Research. 341:1498-1504 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2006.03.028 |
| Popis: | 2-Amino-2,3-dideoxy- d - manno -heptonic acid ( 7 ) has been synthesized from 2,5,6,7-tetra- O -acetyl-3-deoxy- d - gluco -heptono-1,4-lactone ( 1 ), which was readily prepared from d - glycero - d - gulo -heptono-1,4-lactone. O-Deacetylation of 1 followed by treatment with 13:1 (v/v) 2,2-dimethoxypropane/acetone in the presence of p -toluenesulfonic acid gave methyl 3-deoxy-4,5:6,7-di- O -isopropylidene- d - gluco -heptonate ( 3 ) as a crystalline product (80% yield). The free hydroxyl group (OH-2) of 3 was mesylated and substituted by azide to give the corresponding azide derivative 5 . Hydrogenolysis and further hydrolysis of the ester function of 5 afforded α-amino acid 7 (43% overall yield from 1 ). Compound 7 is an analog of l -alanine having a polyhydroxy chain attached to C-3. The diastereoisomer of 7 at C-2, 2-amino-2,3-dideoxy- d - gluco -heptonic acid ( 12 ) was also prepared from 3 , by a route that involved 2,3-dideoxy-2-iodo derivative 8 as a key intermediate. |
| Databáze: | OpenAIRE |
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