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Design, synthesis and characterizati...

Wang, Yimin.

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Design, synthesis and characterization of N3-alkylated cis-syn thymine dimers.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Design, synthesis and characterization of N3-alkylated cis-syn thymine dimers./
Author:	Wang, Yimin.
Description:	223 p.
Notes:	Source: Dissertation Abstracts International, Volume: 66-10, Section: B, page: 5414.
Contained By:	Dissertation Abstracts International66-10B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3191317
ISBN:	9780542345166

Design, synthesis and characterization of N3-alkylated cis-syn thymine dimers.
Wang, Yimin.

Design, synthesis and characterization of N3-alkylated cis-syn thymine dimers. - 223 p.

Source: Dissertation Abstracts International, Volume: 66-10, Section: B, page: 5414.

Thesis (Ph.D.)--Washington University, 2005.

The cis-syn thymine dimer is the major product induced by sunlight and is central to studies of sunlight-induced mutagenesis and skin cancer formation. Existing methods for preparing cis-syn TT dimer suffer from lack of stereocontrol. The stereo selectivity of photodimerization of a series of N-methyl derivatives of protected TT dinucleotide was investigated and found to predominantly favor the cis-syn stereochemistry. Based on these findings a removable trifluoromethylphenyl sulfone auxiliary was developed to control the stereochemistry of the photodimerization reaction. This group was attached to the N3 position of thymidine through a Mitsunobu reaction with 4-trifluoromethylphenyl 2-hydroxylethyl sulfide, and followed by oxidation of the sulfide to the sulfone with mCPBA. Coupling of the modified nucleoside with a standard dT phosphoramidite afforded a dinucleotide building block which showed a high stereoselectivity for cis-syn TT dimer formation. It was then converted to a phosphoramidite and used to synthesize d(CGAAT[cis-syn]TAAGC). The structure and integrity of the cis-syn dimer in the ODN was confirmed by HPLC comparison to an authentic sample and by a nuclease P1 digestion-MS/MS assay.

ISBN: 9780542345166Subjects--Topical Terms:

516206
Chemistry, Organic.

Design, synthesis and characterization of N3-alkylated cis-syn thymine dimers.
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100 1 $a Wang, Yimin. $3 1244027
245 1 0 $a Design, synthesis and characterization of N3-alkylated cis-syn thymine dimers.
300 $a 223 p.
500 $a Source: Dissertation Abstracts International, Volume: 66-10, Section: B, page: 5414.
500 $a Chair: John-Stephen A. Taylor.
502 $a Thesis (Ph.D.)--Washington University, 2005.
520 $a The cis-syn thymine dimer is the major product induced by sunlight and is central to studies of sunlight-induced mutagenesis and skin cancer formation. Existing methods for preparing cis-syn TT dimer suffer from lack of stereocontrol. The stereo selectivity of photodimerization of a series of N-methyl derivatives of protected TT dinucleotide was investigated and found to predominantly favor the cis-syn stereochemistry. Based on these findings a removable trifluoromethylphenyl sulfone auxiliary was developed to control the stereochemistry of the photodimerization reaction. This group was attached to the N3 position of thymidine through a Mitsunobu reaction with 4-trifluoromethylphenyl 2-hydroxylethyl sulfide, and followed by oxidation of the sulfide to the sulfone with mCPBA. Coupling of the modified nucleoside with a standard dT phosphoramidite afforded a dinucleotide building block which showed a high stereoselectivity for cis-syn TT dimer formation. It was then converted to a phosphoramidite and used to synthesize d(CGAAT[cis-syn]TAAGC). The structure and integrity of the cis-syn dimer in the ODN was confirmed by HPLC comparison to an authentic sample and by a nuclease P1 digestion-MS/MS assay.
590 $a School code: 0252.
650 4 $a Chemistry, Organic. $3 516206
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