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Synthesis of the 16-membered BCD ring of complestatin and halogenation of the tryptophan indole
Descriptive
TitleInfo
Title
Synthesis of the 16-membered BCD ring of complestatin and halogenation of the tryptophan indole
Name
(type = personal)
NamePart
(type = family)
Mootoosammy
NamePart
(type = given)
Davena
DisplayForm
Davena Mootoosammy
Role
RoleTerm
(authority = RULIB)
author
Name
(type = personal)
NamePart
(type = family)
Jimenez
NamePart
(type = given)
Leslie
DisplayForm
Leslie Jimenez
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
chair
Name
(type = personal)
NamePart
(type = family)
Hultzsch
NamePart
(type = given)
Kai
DisplayForm
Kai Hultzsch
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
internal member
Name
(type = personal)
NamePart
(type = family)
Taylor
NamePart
(type = given)
John
DisplayForm
John Taylor
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
internal member
Name
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NamePart
Rutgers University
Role
RoleTerm
(authority = RULIB)
degree grantor
Name
(type = corporate)
NamePart
Graduate School - New Brunswick
Role
RoleTerm
(authority = RULIB)
school
TypeOfResource
Text
Genre
(authority = marcgt)
theses
OriginInfo
DateCreated
(qualifier = exact)
2011
DateOther
(qualifier = exact);
(type = degree)
2011-05
Place
PlaceTerm
(type = code)
xx
Language
LanguageTerm
(authority = ISO639-2b);
(type = code)
eng
Abstract
(type = abstract)
Complestatin is a natural product that has demonstrated inhibition activity against HIV-1 integrase and initiation of the complement pathway. Though its biological activity is proven, the total synthesis of the molecule is challenging in many ways. In this thesis the synthetic strategy taken for the partial synthesis of the BCD ring fragment of Complestatin is described. Part of the synthetic studies on the BCD ring involves using the mild conditions to limit isomerization of the sensitive phenylglycine subunits. This was achieved by using DEPBT and HATU as coupling reagents that limit epimerization during condensation. Oxidative phenol coupling is used to form a biaryl ether bond between the L-tyrosine and 4-hydroxyphenylglycine subunits to synthesize the BCD ring. Previous syntheses to form this bond require the functionalization of the subunits. It is our goal to limit the synthesis by decreasing the amount to steps necessary to form the BCD ring, which is accomplished using this method. Our synthesis of the BCD ring is 6 steps from 4-hydroxyphenylglycine, with approximately 10% overall yield. The investigation into the synthesis of Complestatin evolves around the synthesis of 6-bromotryptophan. In order to limit the amount of steps in the total synthesis, the project for the facile synthesis of 6-bromotryptophan was undertaken. It was found that the Boc protecting group on the amino group provided efficient protection of the 2-position on the indole, leading to the formation of 5-bromotryptophan. The synthesis of the TMC-95A southern fragment was also accomplished through a series of peptide couplings.
Subject
(authority = RUETD)
Topic
Chemistry and Chemical Biology
RelatedItem
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TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier
(type = RULIB)
ETD
Identifier
ETD_3340
PhysicalDescription
Form
(authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
xi, 43 p. : ill.
Note
(type = degree)
M.S.
Note
(type = bibliography)
Includes bibliographical references
Note
(type = vita)
Includes vita
Note
(type = statement of responsibility)
by Davena Mootoosammy
Subject
(authority = ETD-LCSH)
Topic
HIV infections--Treatment
Subject
(authority = ETD-LCSH)
Topic
Microbiological synthesis
Identifier
(type = hdl)
http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000061362
RelatedItem
(type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier
(type = local)
rucore19991600001
Location
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(authority = marcorg);
(displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
Identifier
(type = doi)
doi:10.7282/T3Q81CC7
Genre
(authority = ExL-Esploro)
ETD graduate
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Rights
RightsDeclaration
(ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder
(type = personal)
Name
FamilyName
Mootoosammy
GivenName
Davena
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime
(encoding = w3cdtf);
(qualifier = exact);
(point = start)
2011-04-15 16:14:11
AssociatedEntity
Name
Davena Mootoosammy
Role
Copyright holder
Affiliation
Rutgers University. Graduate School - New Brunswick
AssociatedObject
Type
License
Name
Author Agreement License
Detail
I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
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961024
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