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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Precise Installation of Diazo-Tagged Side-Chains on Proteins to Enable In Vitro and In-Cell Site-Specific Labeling

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Author(s):
Bernardim, Barbara [1] ; Dunsmore, Lavinia [1] ; Li, He [1] ; Hocking, Brad [1] ; Nunez-Franco, Reyes [2] ; Navo, Claudio D. [2] ; Jimenez-Oses, Gonzalo [2] ; Burtoloso, Antonio C. B. [3] ; Bernardes, Goncalo J. L. [1, 4]
Total Authors: 9
Affiliation:
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW - England
[2] CIC bioGUNE BRTA, Computat Chem Lab, Derio 48160, Bizkaia - Spain
[3] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13563120 Sao Carlos, SP - Brazil
[4] Univ Lisbon, Fac Med, Inst Med Mol, P-1649028 Lisbon - Portugal
Total Affiliations: 4
Document type: Journal article
Source: BIOCONJUGATE CHEMISTRY; v. 31, n. 6, p. 1604-1610, JUN 2020.
Web of Science Citations: 0
Abstract

The chemistry of diazo compounds has generated a huge breadth of applications in the field of organic synthesis. Their versatility combined with their tunable reactivity, stability, and chemoselectivity makes diazo compounds desirable reagents for chemical biologists. Here, we describe a method for the precise installation of diazo handles on proteins and antibodies in a mild and specific approach. Subsequent 1,3-cycloaddition reactions with strained alkynes enable both bioimaging through an in-cell ``click{''} reaction and probing of the cysteine proteome in cell lysates. The selectivity and efficiency of these processes makes these suitable reagents for chemical biology studies. (AU)

FAPESP's process: 13/25504-1 - Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts
Grantee:Antonio Carlos Bender Burtoloso
Support Opportunities: Regular Research Grants
FAPESP's process: 15/07509-1 - Site-specific modification of proteins via aqueous Horner-Wadsworth-Emmons reaction followed by Wolff rearrangement
Grantee:Barbara Bernardim de Souza
Support Opportunities: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 17/13168-8 - Construction of chemically defined antibody-drug conjugates using carbonylacrylic reagents
Grantee:Barbara Bernardim de Souza
Support Opportunities: Scholarships abroad - Research Internship - Post-doctor