2019
DOI: 10.1002/cbic.201900627
|View full text |Cite
|
Sign up to set email alerts
|

Cycloadditions of Trans‐Cyclooctenes and Nitrones as Tools for Bioorthogonal Labelling

Abstract: Trans‐cyclooctenes (TCOs) represent interesting and highly reactive dipolarophiles for organic transformations including bioorthogonal chemistry. Herein we show that TCOs react rapidly with nitrones and that these reactions are bioorthogonal. Kinetic analysis of acyclic and cyclic nitrones with strained‐trans‐cyclooctene (s‐TCO) shows fast reactivity and demonstrates the utility of this cycloaddition reaction for bioorthogonal labelling. Labelling of the bacterial peptidoglycan layer with unnatural d‐amino aci… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1

Citation Types

0
19
0

Year Published

2020
2020
2024
2024

Publication Types

Select...
6
1

Relationship

2
5

Authors

Journals

citations
Cited by 11 publications
(19 citation statements)
references
References 41 publications
0
19
0
Order By: Relevance
“…The dataset consists of 11 molecules -tetrazine derivatives and 12 moleculescyclooctene derivatives (see supplementary Table A1). All of these bifunctional moieties are non-radioactive parts of modern radiopharmaceuticals responsible for pharmacokinetics and conjugation, able to provide click reaction between each other and bio conjugate through oxime, hydrazone or peptide bonding [33,34]. In the set molecule from C1 to C15 are newly synthesized and the rest are commercially available (see supplementary Table A1).…”
Section: Data Setmentioning
confidence: 99%
“…The dataset consists of 11 molecules -tetrazine derivatives and 12 moleculescyclooctene derivatives (see supplementary Table A1). All of these bifunctional moieties are non-radioactive parts of modern radiopharmaceuticals responsible for pharmacokinetics and conjugation, able to provide click reaction between each other and bio conjugate through oxime, hydrazone or peptide bonding [33,34]. In the set molecule from C1 to C15 are newly synthesized and the rest are commercially available (see supplementary Table A1).…”
Section: Data Setmentioning
confidence: 99%
“…Rate constants were measured previously. 17,23,42,43 of 21.4-23.0 kcal mol À1 , and 1b gave the smallest value. Distortion energy of nitrones also had the smallest value for 1b, suggesting that 1b had the least steric hindrance (entry 2).…”
mentioning
confidence: 95%
“…These include strain-promoted alkynenitrone cycloadditions (SPANC) as well as trans-cyclooctenenitrone ligations that occur selectively and with high reaction velocities. [15][16][17][18][19][20][21][22][23] Furthermore, nitrones provide an added level of versatility in that their reactivity can be tuned stereoelectronically, through substituent effects on both the nitrone nitrogen atom and on the adjacent carbon atoms. This tuneability has enabled duplex labelling experiments with different nitronealkyne pairs.…”
mentioning
confidence: 99%
See 2 more Smart Citations