dc.contributor.author |
Lin Y. |
|
dc.contributor.author |
Vong K. |
|
dc.contributor.author |
Matsuoka K. |
|
dc.contributor.author |
Tanaka K. |
|
dc.date.accessioned |
2019-01-22T20:38:50Z |
|
dc.date.available |
2019-01-22T20:38:50Z |
|
dc.date.issued |
2018 |
|
dc.identifier.issn |
0947-6539 |
|
dc.identifier.uri |
https://dspace.kpfu.ru/xmlui/handle/net/148112 |
|
dc.description.abstract |
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim In previously reported work, AuIIIcomplexes coordinated with 2-benzoylpyridine ligand, BPy-Au, were prebound to a protein and used to discover a novel protein-directed labeling approach with propargyl ester functional groups. In this work, further examination discovered that gold catalysts devoid of the 2-benzoylpyridine ligand (e.g., NaAuCl4) had significantly reduced levels of protein labeling. Mechanistic investigations then revealed that BPy-Au and propargyl esters undergo a rare example of C(sp2)−C(sp) aryl–alkynyl cross-coupling, likely through spontaneous reductive elimination. Overall, these observations appear to suggest that BPy-Au-mediated, propargyl ester-based protein labeling acts via an activated ester intermediate, which contributes to our understanding of this process and will aid the expansion/optimization of gold-catalyst usage in future bioconjugation applications, especially in vivo. |
|
dc.relation.ispartofseries |
Chemistry - A European Journal |
|
dc.subject |
alkynes |
|
dc.subject |
amides |
|
dc.subject |
cross coupling |
|
dc.subject |
gold catalysis |
|
dc.subject |
protein conjugation |
|
dc.title |
2-Benzoylpyridine Ligand Complexation with Gold Critical for Propargyl Ester-Based Protein Labeling |
|
dc.type |
Article |
|
dc.relation.ispartofseries-issue |
42 |
|
dc.relation.ispartofseries-volume |
24 |
|
dc.collection |
Публикации сотрудников КФУ |
|
dc.relation.startpage |
10595 |
|
dc.source.id |
SCOPUS09476539-2018-24-42-SID85050470564 |
|