The synthesis and characterization of some dimethylarsinous acid esters of thio- and selenogalactose /
| Main Author: | |
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| Other Authors: | , , |
| Format: | Thesis Book |
| Language: | English |
| Published: |
[College Station, Tex.] :
Daniel,
1977.
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| Subjects: | |
| Online Access: | Link to ProQuest copy Link to OAKTrust copy |
| Abstract: | A series of galactose derivatives containing the -XAs(CH₃)₂ moiety u (X = S, Se) has been prepared. These are 2 ,3 ,4 ,6-tetra -0 -acetyl-1 -Sdimethylarsino-l-thio- β-D-galactopyranose, 2 ,3 ,4 ,6-tetra-O-acetyl-1 -Sedimethylarsino-l-seleno- β-D-galactopyranose, 1 ,2:3 ,4-di-0-isopropylidene- 6-S-dimethylarsino-6-thio- α-D-galactopyranose, methyl 6-S-dimethylarsino- 6-thio-β--D-galactopyranoside, and 1 ,2:3 ,4-di-0-isopropylidene-6-Se-dimethylarsino-6-seleno- α -D-galactopyranose. Attempted preparations are also reported for 1-Se-dimethylarsino-l-seleno-β-D-galactopyranose and 6-Se-dimethylarsino-6-seleno- β -D-galactopyranose. The ¹H nmr spectra of these compounds may be interpreted in a manner consistent with the proposed structures. In derivatives bearing the -SeAs(CH₃)₂ moiety, the resonances of the arsenic methyl groups show a consistent shift to lower field s when compared with the analogous sulfur-containing compounds. The ultraviolet spectra of these thio - and selenosugars are reported. A slight red shift is noted in the Se-As bonded compounds relative to analogous S-As derivatives. A simplified molecular orbital (MO) argument is used to interpret this shift. The mass spectra of the compounds prepared are reported. In several cases molecular ions are observed. This is noteworthy because the mass spectra of most carbohydrate derivatives do not usually exhibit molecular ions. Mass spectral fragmentation pathways are proposed for both the glycon (sugar) and the aglycon (-XAsMe₂) parts of these compounds. Three of the reported compounds, 2 ,3 ,4 ,6-tetra -0 -acetyl-1 -S-dimethylarsino-1-thio-β-D-galacfopyranose, 1-S-dimethylarsino-1-thio- β-D-galactopyranose, and 1 ,2:3,4-di-0-isopropylidene-6-S-dimethylarsino- 6-thio- α -D-galactopyranose show anti-tumor activity in vivo in mice with lymphocytic leukemia (P388). Compounds of this type may be useful chemotherapeutic agents. |
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| Item Description: | "Major subject: Chemistry." Vita. |
| Physical Description: | xi, 112 leaves : illustrations ; 28 cm |
| Bibliography: | Includes bibliographical references (leaves 103-111). |