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Synthesis of polyhydroxy amino acids based on D- and L-alanine from D-glycero-D-gulo-heptono-1,4-lactone.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Gómez, Romina V. Kolender, Adriana A. Varela, Oscar |
| Copyright Year | 2006 |
| Abstract | 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 alpha-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. |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://digital.bl.fcen.uba.ar/Download/paper/paper_00086215_v341_n10_p1498_Gomez.pdf |
| PubMed reference number | 16618479v1 |
| Volume Number | 341 |
| Issue Number | 10 |
| Journal | Carbohydrate research |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | 2,2-dimethoxypropane Acetone Alanine Amino Acids Amino Acids, Branched-Chain Analog Azides D-Alanine Transaminase Eighty Esters GLUCEPTATE SODIUM Gulo Hydroxyl Radical Methylmethacrylate Thioctic Acid Volume fraction hydroxyl group |
| Content Type | Text |
| Resource Type | Article |
