Synthesis of 4,6‐Difluoro‐Tryptophan as a Probe for Protein 19F NMR

Author:

Monnie Christina M.1,Hernández Iker2,Meléndez‐Pacheco Raixie1,Bhinderwala Fatema1,Soloshonok Vadim A.23ORCID,Gronenborn Angela M.1ORCID,Landa Aitor2ORCID,Oiarbide Mikel2ORCID

Affiliation:

1. Department of Structural Biology University of Pittsburgh School of Medicine 3501 Fifth Ave. Pittsburgh PA 15261 USA

2. Department of Organic Chemistry I Faculty of Chemistry University of the Basque Country UPV/EHU Paseo Manuel Lardizabal 3 20018 Donostia-San Sebastián Spain

3. IKERBASQUE, Basque Foundation for Science Bilbao 48011 Spain

Abstract

AbstractA scalable procedure for the synthesis of 4,6‐difluorotryptophan is reported based on a deaminative coupling of a 4,6‐difluorogramine with 2‐benzylthio‐1,5‐dihydro‐4H‐imidazolone as glycine equivalent. Thus prepared 4,6‐difluorotryptophan was incorporated into the C‐terminal domain of the HIV‐1 capsid protein (CA‐CTD), and 19F spectra of the 4,6‐difluoro Trp CA CTD were recorded and compared to the singly fluorinated counterparts.

Funder

Eusko Jaurlaritza

University of Pittsburgh

National Institutes of Health

Publisher

Wiley

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