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

被引：1

作者：

Monnie, Christina M. ^{[1
]}

Hernandez, Iker ^{[2
]}

Melendez-Pacheco, Raixie ^{[1
]}

Bhinderwala, Fatema ^{[1
]}

Soloshonok, Vadim A. ^{[2
,3
]}

Gronenborn, Angela M. ^{[1
]}

Landa, Aitor ^{[2
]}

Oiarbide, Mikel ^{[2
]}

机构：

[1] Univ Pittsburgh, Dept Struct Biol, Sch Med, 3501 Fifth Ave, Pittsburgh, PA 15261 USA

[2] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, Donostia San Sebastian 20018, Spain

[3] Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 16期

关键词：

Fluorinated tryptophans; Amino acid synthesis; Gramines coupling; Protein F-19 NMR; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; CHEMISTRY; HYDANTOINS; ESTERS;

D O I：

10.1002/adsc.202400031

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A 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 F-19 spectra of the 4,6-difluoro Trp CA CTD were recorded and compared to the singly fluorinated counterparts.

引用

页码：3417 / 3422

页数：6

共 50 条

[1] The difluoromethyl group as a 19F NMR probe of protein structure and function
Vaughan, MD
Cleve, P
Robinson, V
Daub, E
Honek, JF
FASEB JOURNAL, 1999, 13 (07): : A1383 - A1383
[2] 19F NMR studies of tryptophan/serum albumin binding
Cao, BL
Endsley, S
Andersen, NH
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (01) : 69 - 75
[3] 19F: A small probe for a giant protein
Cosottini, Lucrezia
Zineddu, Stefano
Massai, Lara
Ghini, Veronica
Turano, Paola
JOURNAL OF INORGANIC BIOCHEMISTRY, 2023, 244
[4] Protein 19F NMR in Escherichia coli
Li, Conggang
Wang, Gui-Fang
Wang, Yaqiang
Creager-Allen, Rachel
Lutz, Evan A.
Scronce, Heidi
Slade, Kristin M.
Ruf, Rebecca A. S.
Mehl, Ryan A.
Pielak, Gary J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (01) : 321 - 327
[5] 4′-Fluorinated RNA: Synthesis, Structure, and Applications as a Sensitive 19F NMR Probe of RNA Structure and Function
Li, Qiang
Chen, Jialiang
Trajkovski, Marko
Zhou, Yifei
Fan, Chaochao
Lu, Kuan
Tang, Pingping
Su, Xuncheng
Plavec, Janez
Xi, Zhen
Zhou, Chuanzheng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (10) : 4739 - 4748
[6] A Genetically Encoded 19F NMR Probe for Tyrosine Phosphorylation
Li, Fahui
Shi, Pan
Li, Jiasong
Yang, Fan
Wang, Tianyuan
Zhang, Wei
Gao, Feng
Ding, Wei
Li, Dong
Li, Juan
Xiong, Ying
Sun, Jinpeng
Gong, Weimin
Tian, Changlin
Wang, Jiangyun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) : 3958 - 3962
[7] Use of 19F NMR to probe conformational changes of arrestin
Stout, Rebecca Mae
Zhan, Xuanzhi
Carroll, William
FASEB JOURNAL, 2018, 32 (01):
[8] Ex Vivo Analysis of Tryptophan Metabolism Using 19F NMR
Tombari, Robert J.
Saunders, Carla M.
Wu, Chun-Yi
Dunlap, Lee E.
Tantillo, Dean J.
Olson, David E.
ACS CHEMICAL BIOLOGY, 2019, 14 (09) : 1866 - 1873
[9] 4,4-Difluoroproline as a Unique 19F NMR Probe of Proline Conformation
Ganguly, Himal K.
Ludwig, Brice A.
Tressler, Caitlin M.
Bhatt, Megh R.
Pandey, Anil K.
Quinn, Caitlin M.
Bai, Shi
Yap, Glenn P. A.
Zondlo, Neal J.
BIOCHEMISTRY, 2024, 63 (09) : 1131 - 1146
[10] A genetically encoded 19F NMR probe for lysine acetylation
Zhang, Feng
Zhou, Qing
Yang, Guiwen
An, Liguo
Li, Fahui
Wang, Jiangyun
CHEMICAL COMMUNICATIONS, 2018, 54 (31) : 3879 - 3882

← 1 2 3 4 5 →