A novel acyl protecting group for cytosine and adenine has been prepared
from 4-( chloromethyl) benzoic acid. Reaction of the acid with morpholine produces
4-( 4-morpholinyl )methyl benzoic acid which is converted to it's acid chloride
with thionyl chloride. This may be used to acylate cytidine and adenosine under
standard conditions. This ionizable protecting group has the ability to solublize
protected oligomers, which allows their purification with ion-exchange chromatography
on S-Sepharose. Solid phase synthesis has been performed using this protecting
group on morpholine nucleosides. Morpholine nucleoside carbamates were
synthesized in high yields. The results revealed that high purities of the hexamers
were obtained. These hexamers, which have the protecting groups intact, provide
the potential for further segment condensation to make large size oligonucleotide
analogues.
The success of the solid phase synthesis was dependent upon use of a selectively
cleavable anchor which allowed the finished oligomer to be released from the resin
with protecting groups intact. Attempts to modify the anchor to make it more efficient
were unsuccessful. It was found that DBU degrades derivatized polystyrene
resin and should not be used at early stages in solid phase synthesis. / Graduation date: 1992
| Identifer | oai:union.ndltd.org:ORGSU/oai:ir.library.oregonstate.edu:1957/37367 |
| Date | 26 November 1991 |
| Creators | Wang, Haiyan, 1963- |
| Contributors | Weller, Dwight D. |
| Source Sets | Oregon State University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis/Dissertation |
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