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  

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Control Number  

joongbu:658131