Design and Synthesis of New Classes of Heterocyclic C-Glycoconjugates and Carbon-Linked Sugar and Heterocyclic Amino Acids by Asymmetric Multicomponent Reactions (AMCRs)

ChemInform ◽  
2006 ◽  
Vol 37 (41) ◽  
Author(s):  
Alessandro Dondoni ◽  
Alessandro Massi
Keyword(s):  
Amino Acids ◽  
Multicomponent Reactions ◽  
Design And Synthesis

Selected Research Topics of the Dondoni Group over the Last Two Decades (2000–2020)

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1361-1371 ◽  
Author(s):  
Alessandro Dondoni
Keyword(s):  
Amino Acids ◽  
Bioorganic Chemistry ◽  
Multicomponent Reactions ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Research Topics ◽  
Main Target ◽  
Sulfur Fluoride ◽  
Primary Rule ◽  
Selection Of

From a selection of research topics carried out in our laboratory during the last twenty years it becomes apparent that our main target was the discovery of new or improved synthetic methods together with new properties. Our efforts were made with the aim of being of some utility to other fields of research, with particular emphasis to glycobiology and heterocyle-based bioorganic chemistry. We performed new chemistry mainly in the field of carbohydrate manipulations taking as a primary rule the simplicity and efficiency manners. Toward this end, modern synthetic tools and approaches were employed such as heterocyle-based transformations, multicomponent reactions, organocatalysis, click azide–alkyne cycloadditions, reactions in ionic liquids, click photoinduced thiol-ene coupling, and click sulfur–fluoride exchange chemistry. With these potent methodologies in hand, the syntheses of carbohydrate containing amino acids up to proteins glycosylation were performed.1 Heterocyclic Glycoconjugates and Amino Acids2 Triazole-Linked Oligonucleotides: Application of Click CuAAC3 Non-Natural Glycosyl Amino Acids4 Non-Natural Oligosaccharides5 Calixarene-Based Glycoclusters6 Carbohydrate-Based Building Blocks7 Homoazasugars and Aza-C-disaccharides8 Synthesis of Glycodendrimers9 Peptide and Protein Glycoconjugates10 Conclusions

Molecular Design and Synthesis of Artificial Ion Channels Based on Cyclic Peptides Containing Unnatural Amino Acids

2001 ◽  
Vol 66 (9) ◽  
pp. 2978-2989 ◽  
Author(s):  
Hitoshi Ishida ◽  
Zhi Qi ◽  
Masahiro Sokabe ◽  
Kiyoshi Donowaki ◽  
Yoshihisa Inoue
Keyword(s):  
Amino Acids ◽  
Ion Channels ◽  
Unnatural Amino Acids ◽  
Cyclic Peptides ◽  
Molecular Design ◽  
Design And Synthesis

scholarly journals Rational Design and Synthesis of Novel Dual Protacs for Simultaneous Degradation of EGFR and PARP

2021 ◽  
Author(s):  
Mengzhu Zheng ◽  
Junfeng Huo ◽  
Xiaoxia Gu ◽  
Canrong Wu ◽  
Qingzhe Zhang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Drug Discovery ◽  
Rational Design ◽  
Bispecific Antibodies ◽  
Design And Synthesis ◽  
Synthetic Strategy ◽  
Dual Targeting ◽  
Different Types ◽  
Natural Amino Acids ◽  
Simultaneous Degradation

Inspired by the success of dual targeting drugs, especially bispecific antibodies, we propose to combine the concept of protac and dual targeting to design and synthesize dual protac molecules with the function of degrading two completely different types of targets simultaneously. A library of novel dual targeting protac molecules have been rationally designed and prepared. A convergent synthetic strategy has been utilized to achieve high synthetic efficiency. These dual protac structures are characterized by using trifunctional natural amino acids as star-type core linkers to connect two independent inhibitors and E3 ligands together. In this study, gefitinib, olaparib, and CRBN or VHL E3 ligand were used as substrates to synthesize novel dual protacs. They successfully degraded both EGFR and PARP simultaneously in cancer cells. Being the first successful example of dual protacs, this technique will greatly widen the range of application of the protac method and open up a new field for drug discovery.

scholarly journals Steroid diversification by multicomponent reactions

2019 ◽  
Vol 15 ◽  
pp. 1236-1256 ◽  
Author(s):  
Leslie Reguera ◽  
Cecilia I Attorresi ◽  
Javier A Ramírez ◽  
Daniel G Rivera
Keyword(s):  
Amino Acids ◽  
Drug Discovery ◽  
Carboxylic Acid ◽  
Supramolecular Chemistry ◽  
Boronic Acid ◽  
Chemical Biology ◽  
Multicomponent Reactions ◽  
Naturally Occurring ◽  
Almost All ◽  
Structural Diversification

Reports on structural diversification of steroids by means of multicomponent reactions (MCRs) have significantly increased over the last decade. This review covers the most relevant strategies dealing with the use of steroidal substrates in MCRs, including the synthesis of steroidal heterocycles and macrocycles as well as the conjugation of steroids to amino acids, peptides and carbohydrates. We demonstrate that steroids are available with almost all types of MCR reactive functionalities, e.g., carbonyl, carboxylic acid, alkyne, amine, isocyanide, boronic acid, etc., and that steroids are suitable starting materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and supramolecular chemistry applications.

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