RUcore: Rutgers University Community Repository
The total synthesis of mycothiol and new inhibitors of carbohydrate processing enzymes
Descriptive
TypeOfResource
Text
TitleInfo
(ID = T-1)
Title
The total synthesis of mycothiol and new inhibitors of carbohydrate processing enzymes
Identifier
ETD_2617
Identifier
(type = hdl)
http://hdl.rutgers.edu/1782.2/rucore10001600001.ETD.000052975
Language
LanguageTerm
(authority = ISO639-2);
(type = code)
eng
Genre
(authority = marcgt)
theses
Subject
(ID = SBJ-1);
(authority = RUETD)
Topic
Chemistry and Chemical Biology
Subject
(ID = SBJ-2);
(authority = ETD-LCSH)
Topic
Carbohydrates--Metabolism
Subject
(ID = SBJ-3);
(authority = ETD-LCSH)
Topic
Glycosidases
Subject
(ID = SBJ-4);
(authority = ETD-LCSH)
Topic
Enzymes--Biotechnology
Abstract
(type = abstract)
The work described in this dissertation covers a wide range of disciplines within organic chemistry, with the common goal of obtaining more information about various carbohydrate-processing enzymes. Carbohydrate-processing enzymes are garnering an increasing amount of attention relative to their more well-studied protein-processing counterparts, as they are ubiquitous and implicated in various regulatory, signaling and metabolic processes in eukaryotic cells. Chapter 1 involves the synthesis of anomeric phosphothioates as possible O-GlcNAc transferase inhibitors, and a mechanistic study on the anomeric Pudovik rearrangement of thiophosphites to thiophosphonates is described. Chapter 2 is an account of the development of a facile method for functionalizing 2-methyl thiazoline rings, and several selective GlcNAc-thiazoline-based O-GlcNAcase inhibitors were synthesized by this method. Chapter 3 details the 16-step total synthesis of the M. tuberculosis antioxidant carbohydrate mycothiol by a new intramolecular glycosylation method. The method is amenable to glycosylations of 2-deoxy-2-aminoglyosides, a unique aspect among such reactions. The efficiency of the synthetic route to mycothiol makes it attractive as a template from which to design analogs as potential inhibitors of enzymes involved in the biosynthesis of mycothiol. An apparently unprecedented 1,9-hydride shift is also described in the third chapter. Chapter 4 describes a tripartate prolonged-release drug delivery system, in which the drug of interest (ethynyl estradiol in this study) is coupled, through a variable linker, to another carrier drug with a long half-life and a relatively high inhibitory concentration. The effect of steric bulk on the in vitro release of ethynyl estradiol was evaluated, showing a direct relationship between steric bulk around the ester linkage and ethynyl estradiol release time. In vivo data from pigs also seemed to point to an increase in drug bioavailability with the 3-part system. Finally, chapter 5 describes early efforts to synthesize boronic acid analogs of folic acid and antifolates.
PhysicalDescription
Form
(authority = gmd)
electronic resource
Extent
xvi, 267 p. : ill.
InternetMediaType
application/pdf
InternetMediaType
text/xml
Note
(type = degree)
Ph.D.
Note
Includes abstract
Note
Vita
Note
(type = bibliography)
Includes bibliographical references
Note
(type = statement of responsibility)
by Kehinde Ajayi
Name
(ID = NAME-1);
(type = personal)
NamePart
(type = family)
Ajayi
NamePart
(type = given)
Kehinde
NamePart
(type = date)
1979-
Role
RoleTerm
(authority = RULIB)
author
DisplayForm
Kehinde Ajayi
Name
(ID = NAME-2);
(type = personal)
NamePart
(type = family)
Knapp
NamePart
(type = given)
Spencer
Role
RoleTerm
(authority = RULIB)
chair
Affiliation
Advisory Committee
DisplayForm
Spencer Knapp
Name
(ID = NAME-3);
(type = personal)
NamePart
(type = family)
Williams
NamePart
(type = given)
Lawrence
Role
RoleTerm
(authority = RULIB)
internal member
Affiliation
Advisory Committee
DisplayForm
Lawrence Williams
Name
(ID = NAME-4);
(type = personal)
NamePart
(type = family)
Seidel
NamePart
(type = given)
Daniel
Role
RoleTerm
(authority = RULIB)
internal member
Affiliation
Advisory Committee
DisplayForm
Daniel Seidel
Name
(ID = NAME-5);
(type = personal)
NamePart
(type = family)
Kydonieus
NamePart
(type = given)
Agis
Role
RoleTerm
(authority = RULIB)
outside member
Affiliation
Advisory Committee
DisplayForm
Agis Kydonieus
Name
(ID = NAME-1);
(type = corporate)
NamePart
Rutgers University
Role
RoleTerm
(authority = RULIB)
degree grantor
Name
(ID = NAME-2);
(type = corporate)
NamePart
Graduate School - New Brunswick
Role
RoleTerm
(authority = RULIB)
school
OriginInfo
DateCreated
(qualifier = exact)
2010
DateOther
(qualifier = exact);
(type = degree)
2010
Place
PlaceTerm
(type = code)
xx
Location
PhysicalLocation
(authority = marcorg);
(displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
RelatedItem
(type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier
(type = RULIB)
ETD
RelatedItem
(type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier
(type = local)
rucore19991600001
Identifier
(type = doi)
doi:10.7282/T3QV3MMW
Genre
(authority = ExL-Esploro)
ETD doctoral
Back to the top
Rights
RightsDeclaration
(AUTHORITY = GS);
(ID = rulibRdec0006)
The author owns the copyright to this work.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
RightsHolder
(ID = PRH-1);
(type = personal)
Name
FamilyName
Ajayi
GivenName
Kehinde
Role
Copyright Holder
RightsEvent
(ID = RE-1);
(AUTHORITY = rulib)
Type
Permission or license
DateTime
2010-04-15 02:08:58
AssociatedEntity
(ID = AE-1);
(AUTHORITY = rulib)
Role
Copyright holder
Name
Kehinde Ajayi
Affiliation
Rutgers University. Graduate School - New Brunswick
AssociatedObject
(ID = AO-1);
(AUTHORITY = rulib)
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.
RightsEvent
(ID = RE-2);
(AUTHORITY = rulib)
Type
Embargo
DateTime
2010-05-31
Detail
Access to this PDF has been restricted at the author's request. It will be publicly available after May 30th, 2012.
Back to the top
Technical
ContentModel
ETD
MimeType
(TYPE = file)
application/pdf
MimeType
(TYPE = container)
application/x-tar
FileSize
(UNIT = bytes)
15820800
Checksum
(METHOD = SHA1)
5470e682c973d3f2101d39d8664ac1883cbeaad7
Back to the top
Statistical Profile