Synthetic Tools that Enable Synthesis and Understanding of Bioactive Macrocycles

被引：0
作者：
Yudin, Andrei K. [1 ]
机构：
[1] Univ Toronto, Davenport Res Labs, 80 St George St, Toronto, ON M6S 3H6, Canada
来源：
SYNLETT | 2022年 / 33卷 / 19期
关键词：
macrocycles; peptides; cellular permeability; heterocycles; amphoteric molecules; CIS-TRANS ISOMERIZATION;
D O I：
10.1055/a-1892-9671
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This article aims to summarizing the evolution of my lab's research efforts in making arid understanding peptide macrocycles. What started as a curiosity-driven investigation of amphoteric structures in multicomponent reactions, has turned into a sustained exploration of complex macrocyclic peptides. As part of this journey, my students and I have introduced new tools that enable chemical synthesis and property-driven optimization of cyclic peptides. These contributions are expected to be relevant in the areas of drug discovery and biological probe design.
引用
收藏
页码：1884 / 1889
页数：6
相关论文
共 27 条
  • [1] NUCLEAR MAGNETIC RESONANCE SPECTRA AND NITROGEN INVERSION IN 1-ACYLAZIRIDINES
    ANET, FAL
    OSYANY, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) : 352 - &
  • [2] Conformational Control of Macrocycles by Remote Structural Modification
    Appavoo, Solomon D.
    Huh, Sungjoon
    Diaz, Diego B.
    Yudin, Andrei K.
    [J]. CHEMICAL REVIEWS, 2019, 119 (17) : 9724 - 9752
  • [3] Development of Endocyclic Control Elements for Peptide Macrocycles
    Appavoo, Solomon D.
    Kaji, Takuya
    Frost, John R.
    Scully, Conor C. G.
    Yudin, Andrei K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (28) : 8763 - 8770
  • [4] A Mechanistic Model for the Aziridine Aldehyde-Driven Macrocyclization of Peptides
    Belding, Lee
    Zaretsky, Serge
    Yudin, Andrei K.
    Dudding, Travis
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) : 9119 - 9124
  • [5] REACTION OF 1-ACYLAZIRIDINES WITH LITHIUM ALUMINUM HYDRIDE-A NEW ALDEHYDE SYNTHESIS
    BROWN, HC
    TSUKAMOTO, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (08) : 2016 - &
  • [6] The reactivity and conformational control of cyclic tetrapeptides derived from aziridine-containing amino acids
    Chung, Benjamin K. W.
    White, Christopher J.
    Scully, Conor C. G.
    Yudin, Andrei K.
    [J]. CHEMICAL SCIENCE, 2016, 7 (11) : 6662 - 6668
  • [7] Illuminating the dark conformational space of macrocycles using dominant rotors
    Diaz, Diego B.
    Appavoo, Solomon D.
    Bogdanchikova, Anastasia F.
    Lebedev, Yury
    McTiernan, Timothy J.
    dos Passos Gomes, Gabriel
    Yudin, Andrei K.
    [J]. NATURE CHEMISTRY, 2021, 13 (03) : 218 - +
  • [8] Cis-trans isomerization of organic molecules and biomolecules: Implications and applications
    Dugave, C
    Demange, L
    [J]. CHEMICAL REVIEWS, 2003, 103 (07) : 2475 - 2532
  • [9] Frost JR, 2016, NAT CHEM, V8, P1105, DOI [10.1038/NCHEM.2636, 10.1038/nchem.2636]
  • [10] Experiments and Theory in the Preparative Sciences
    Goodwin, William
    [J]. PHILOSOPHY OF SCIENCE, 2012, 79 (04) : 429 - 447
123