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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 서양
- 최종처리일시
- 20250211152815
- ISBN
- 9798384058045
- DDC
- 547
- 서명/저자
- Rh(III)-Catalyzed Methodologies Applied to the Synthesis of Unnatural Peptides
- 발행사항
- [Sl] : Columbia University, 2024
- 발행사항
- Ann Arbor : ProQuest Dissertations & Theses, 2024
- 형태사항
- 192 p
- 주기사항
- Source: Dissertations Abstracts International, Volume: 86-03, Section: B.
- 주기사항
- Advisor: Rovis, Tomislav.
- 학위논문주기
- Thesis (Ph.D.)--Columbia University, 2024.
- 초록/해제
- 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.
- 일반주제명
- Organic chemistry
- 일반주제명
- Biochemistry
- 일반주제명
- Chemistry
- 키워드
- Carboamidation
- 키워드
- Catalysis
- 키워드
- Macrocycles
- 키워드
- Mechanism
- 키워드
- Peptides
- 키워드
- Rhodium
- 기타저자
- Columbia University Chemistry
- 기본자료저록
- Dissertations Abstracts International. 86-03B.
- 전자적 위치 및 접속
- 로그인 후 원문을 볼 수 있습니다.
MARC
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■00520250211152815
■006m o d
■007cr#unu||||||||
■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[Sl]▼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.
