Bioorthogonal chemistry

SL Scinto, DA Bilodeau, R Hincapie, W Lee… - Nature Reviews …, 2021 - nature.com
Bioorthogonal chemistry represents a class of high-yielding chemical reactions that proceed
rapidly and selectively in biological environments without side reactions towards …

Leveraging fleeting strained intermediates to access complex scaffolds

SM Anthony, LG Wonilowicz, MS McVeigh, NK Garg - JACS Au, 2021 - ACS Publications
Arynes, strained cyclic alkynes, and strained cyclic allenes were validated as plausible
intermediates in the 1950s and 1960s. Despite initially being considered mere scientific …

Bioconjugation in materials science

C Bednarek, U Schepers, F Thomas… - Advanced Functional …, 2024 - Wiley Online Library
With the advent of bioconjugation chemistry in the last two decades, highlighted by the
Nobel Prize 2022, the quest for possible novel applications has been greatly intensified …

Heterocycloalkynes fused to a heterocyclic core: searching for an island with optimal stability-reactivity balance

NA Danilkina, AI Govdi, AF Khlebnikov… - Journal of the …, 2021 - ACS Publications
In the search for fundamentally new, active, stable, and readily synthetically accessible
cycloalkynes as strain-promoted azide–alkyne cycloaddition (SPAAC) reagents for …

Rhodium-Catalyzed [7+ 1] Cycloaddition of Exocyclic 1, 3-Dienylcyclopropanes and Carbon Monoxide

Z Huang, X Wang, Y Jin, Z Wang, ZX Yu - Organic Letters, 2023 - ACS Publications
A rhodium-catalyzed [7+ 1] reaction of exocyclic 1, 3-dienylcyclopropanes and carbon
monoxide has been developed to synthesize eight-membered carbocycle-embedded …

Cycloadditions of oxacyclic allenes and a catalytic asymmetric entryway to enantioenriched cyclic allenes

MM Yamano, RR Knapp, A Ngamnithiporn… - Angewandte …, 2019 - Wiley Online Library
The chemistry of strained cyclic alkynes has undergone a renaissance over the past two
decades. However, a related species, strained cyclic allenes, especially heterocyclic …

Synthesis of a New Family of 1, 1-Diazidoethenes: One-Pot Construction of 4-Azido-1, 2, 3-triazoles via Nitrene Cyclization

AV Shastin, BD Tsyrenova, PG Sergeev… - Organic …, 2018 - ACS Publications
The reaction of 4, 4-dichloro-1, 2-diazabuta-1, 3-dienes with sodium azide has been studied
and found to provide straightforward access to extremely rare 1, 1-bisazides. It was …

Taming the reactivity of alkyl azides by intramolecular hydrogen bonding: site-selective conjugation of unhindered diazides

K Maegawa, H Tanimoto, S Onishi… - Organic Chemistry …, 2021 - pubs.rsc.org
Organic azides are still in the center of click chemistry connecting two molecules. However,
taming the conjugation selectivity of azides is difficult without the help of bulky groups. We …

Site-selective conversion of azido groups at carbonyl α-positions to diazo groups in diazido and triazido compounds

T Yokoi, H Tanimoto, T Ueda, T Morimoto… - The Journal of …, 2018 - ACS Publications
This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-
position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone …

Spot the difference in reactivity: a comprehensive review of site-selective multicomponent conjugation exploiting multi-azide compounds

H Tanimoto, T Tomohiro - Chemical Communications, 2024 - pubs.rsc.org
Going beyond the conventional approach of pairwise conjugation between two molecules,
the integration of multiple components onto a central scaffold molecule is essential for the …