| LDR | | 00000nam u2200205 4500 |
| 001 | | 000000432676 |
| 005 | | 20200224133636 |
| 008 | | 200131s2019 ||||||||||||||||| ||eng d |
| 020 | |
▼a 9781687912893 |
| 035 | |
▼a (MiAaPQ)AAI13899528 |
| 040 | |
▼a MiAaPQ
▼c MiAaPQ
▼d 247004 |
| 082 | 0 |
▼a 547 |
| 100 | 1 |
▼a Sutyak, Keith Brandon. |
| 245 | 10 |
▼a 5-Modified Lipophilic G-Quadruplexes: Structural Studies and Applications as Scaffolds for [2+2] Photocycloadditions. |
| 260 | |
▼a [S.l.]:
▼b University of Maryland, College Park.,
▼c 2019. |
| 260 | 1 |
▼a Ann Arbor:
▼b ProQuest Dissertations & Theses,
▼c 2019. |
| 300 | |
▼a 263 p. |
| 500 | |
▼a Source: Dissertations Abstracts International, Volume: 81-05, Section: B. |
| 500 | |
▼a Advisor: Davis, Jeffery T. |
| 502 | 1 |
▼a Thesis (Ph.D.)--University of Maryland, College Park, 2019. |
| 506 | |
▼a This item must not be sold to any third party vendors. |
| 506 | |
▼a This item must not be added to any third party search indexes. |
| 520 | |
▼a Guanosine self-assembly is a powerful tool for constructing nanostructures and materials with intriguing properties. Guanosine's nucleobase has a hydrogen bond donor and acceptor face that in the presence of an appropriate templating cation can self-assemble to form larger G-quadruplex structures. Through the addition of a nonpolar solubilizing group on the 2, 3, or 5 position of guanosine's ribose sugar, the G-quadruplex may be formed in organic solvents. Not surprisingly, any modification made to the guanine nucleobase can have a substantial effect on the self-assembly of the G-quadruplex core. These alterations can significantly alter or destroy the ability of the guanine base to form larger H-bond structures. For this reason, a major target for the synthetic modification of the G-quadruplex is the ribose sugar. Modifications to the sugar can be used to add new functionality or groups capable of modulating the G-quadruplexes stability and structure.The 5-position is easily esterified and is an ideal target for incorporating new functionality to the G-quadruplex, not not much was known about how esterification of the 5-position of guanosine impacted self-assembly. In this thesis, a series of 5-modified aryl esters of guanosine were synthesized G 21-G 25, comprising either activating or de-activating substituents on the aromatic rings, to systematically investigate how the addition of an ester to the 5- position of guanosine affects the self-assembly G-quadruplex. The identity of the 5-aryl ester was found to have a direct impact on the molecularity (how many Gs are in each assembly) and stability of the G-quadruplexes. The information gained from these experiments was applied to rationally design a new G-quadruplex capable of templating a [2+2] photocycloaddition reaction.With an increased knowledge of how modifications to the 5-position affect the structural integrity of the G-quadruplex, we applied this information to rationally design a new G-quadruplex system capable of templating a [2+2] photocycloaddition reaction. To achieve this goal a series of 5-cinnamate esters G 26-G 29 were synthesized and studied. Each derivative G 26- G 29 when self-assembled into a G-quadruplex an photoirradiated underwent a photocycloadditon reaction ins high yields with good stereoselectivity. These same compounds when disassembled only underwent trans-cis photoisomerization. Highlighting the need for the G-quadruplex self-assembly. |
| 590 | |
▼a School code: 0117. |
| 650 | 4 |
▼a Organic chemistry. |
| 690 | |
▼a 0490 |
| 710 | 20 |
▼a University of Maryland, College Park.
▼b Chemistry. |
| 773 | 0 |
▼t Dissertations Abstracts International
▼g 81-05B. |
| 773 | |
▼t Dissertation Abstract International |
| 790 | |
▼a 0117 |
| 791 | |
▼a Ph.D. |
| 792 | |
▼a 2019 |
| 793 | |
▼a English |
| 856 | 40 |
▼u http://www.riss.kr/pdu/ddodLink.do?id=T15492068
▼n KERIS
▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다. |
| 980 | |
▼a 202002
▼f 2020 |
| 990 | |
▼a ***1008102 |
| 991 | |
▼a E-BOOK |