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Rh(III)-Catalyzed Methodologies Applied to the Synthesis of Unnatural Peptides.
Rh(III)-Catalyzed Methodologies Applied to the Synthesis of Unnatural Peptides.
상세정보
- 자료유형
- 학위논문
- Control Number
- 0017163965
- International Standard Book Number
- 9798384058045
- Dewey Decimal Classification Number
- 547
- Main Entry-Personal Name
- Lamartina, Christopher William.
- Publication, Distribution, etc. (Imprint
- [S.l.] : Columbia University., 2024
- Publication, Distribution, etc. (Imprint
- Ann Arbor : ProQuest Dissertations & Theses, 2024
- Physical Description
- 192 p.
- General Note
- Source: Dissertations Abstracts International, Volume: 86-03, Section: B.
- General Note
- Advisor: Rovis, Tomislav.
- Dissertation Note
- Thesis (Ph.D.)--Columbia University, 2024.
- Summary, Etc.
- 요약Contemporary developments in the field of synthetic peptide methodologies are imperative for enabling the advance of drug design in medicinal chemistry. Although many groundbreaking discoveries have been made in this field in the past few decades, there has only been a recent renaissance in transition metal catalyzed methods which create unnatural amino acids and generate macrocyclic peptide structures. Rh(III)-catalyzed methods which install C-C bonds and C-N bonds across readily available alkene substrates have been an underexplored avenue for peptide modification chemistry. In this thesis, several novel catalytic methodologies are disclosed which simultaneously install unnatural amino acid motifs during peptide ligation events. In Chapter 3, we report a modular peptide ligation methodology that couples dioxazolones, arylboronic acids, and acrylamides to construct amide bonds in a diastereoselective manner under mild conditions, facilitated by Rh(III) catalysis. In Chapter 4, we disclose a Rh(III)-catalyzed macrocyclization via carboamidation, reacting acryloyl-peptide-dioxazolone precursors and arylboronic acids to form complex cyclic peptides with concomitant incorporation of noncanonical α-amino acids. In Chapter 5, we describe ongoing efforts to develop a complementary Rh(III)-catalyzed hydroamidation reaction which furnishes macrocyclic peptides to expand the chemical space in which complex peptidomimetic molecules can be attained.
- Subject Added Entry-Topical Term
- Organic chemistry.
- Subject Added Entry-Topical Term
- Biochemistry.
- Subject Added Entry-Topical Term
- Chemistry.
- Index Term-Uncontrolled
- Carboamidation
- Index Term-Uncontrolled
- Catalysis
- Index Term-Uncontrolled
- Macrocycles
- Index Term-Uncontrolled
- Mechanism
- Index Term-Uncontrolled
- Peptides
- Index Term-Uncontrolled
- Rhodium
- Added Entry-Corporate Name
- Columbia University Chemistry
- Host Item Entry
- Dissertations Abstracts International. 86-03B.
- Electronic Location and Access
- 로그인을 한후 보실 수 있는 자료입니다.
- Control Number
- joongbu:658131
MARC
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■020 ▼a9798384058045
■035 ▼a(MiAaPQ)AAI31558602
■040 ▼aMiAaPQ▼cMiAaPQ
■0820 ▼a547
■1001 ▼aLamartina, Christopher William.
■24510▼aRh(III)-Catalyzed Methodologies Applied to the Synthesis of Unnatural Peptides.
■260 ▼a[S.l.]▼bColumbia University. ▼c2024
■260 1▼aAnn Arbor▼bProQuest Dissertations & Theses▼c2024
■300 ▼a192 p.
■500 ▼aSource: Dissertations Abstracts International, Volume: 86-03, Section: B.
■500 ▼aAdvisor: Rovis, Tomislav.
■5021 ▼aThesis (Ph.D.)--Columbia University, 2024.
■520 ▼aContemporary developments in the field of synthetic peptide methodologies are imperative for enabling the advance of drug design in medicinal chemistry. Although many groundbreaking discoveries have been made in this field in the past few decades, there has only been a recent renaissance in transition metal catalyzed methods which create unnatural amino acids and generate macrocyclic peptide structures. Rh(III)-catalyzed methods which install C-C bonds and C-N bonds across readily available alkene substrates have been an underexplored avenue for peptide modification chemistry. In this thesis, several novel catalytic methodologies are disclosed which simultaneously install unnatural amino acid motifs during peptide ligation events. In Chapter 3, we report a modular peptide ligation methodology that couples dioxazolones, arylboronic acids, and acrylamides to construct amide bonds in a diastereoselective manner under mild conditions, facilitated by Rh(III) catalysis. In Chapter 4, we disclose a Rh(III)-catalyzed macrocyclization via carboamidation, reacting acryloyl-peptide-dioxazolone precursors and arylboronic acids to form complex cyclic peptides with concomitant incorporation of noncanonical α-amino acids. In Chapter 5, we describe ongoing efforts to develop a complementary Rh(III)-catalyzed hydroamidation reaction which furnishes macrocyclic peptides to expand the chemical space in which complex peptidomimetic molecules can be attained.
■590 ▼aSchool code: 0054.
■650 4▼aOrganic chemistry.
■650 4▼aBiochemistry.
■650 4▼aChemistry.
■653 ▼aCarboamidation
■653 ▼aCatalysis
■653 ▼aMacrocycles
■653 ▼aMechanism
■653 ▼aPeptides
■653 ▼aRhodium
■690 ▼a0490
■690 ▼a0487
■690 ▼a0485
■71020▼aColumbia University▼bChemistry.
■7730 ▼tDissertations Abstracts International▼g86-03B.
■790 ▼a0054
■791 ▼aPh.D.
■792 ▼a2024
■793 ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17163965▼nKERIS▼z이 자료의 원문은 한국교육학술정보원에서 제공합니다.
