Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in 19F NMR

被引：23

作者：

Qin, Luoheng ^{[1
]}

Sheridan, Christopher ^{[1
]}

Gao, Jianmin ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 02期

基金：

美国国家科学基金会;

关键词：

PROTEIN-STRUCTURE; COILED-COIL; PEPTIDE; DESIGN; REAGENT; BINDING;

D O I：

10.1021/ol203140n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorinated amino acids serve as powerful tools in protein chemistry. We synthesized a series of pare-substituted tetrafluorophenylalanines via the regioselective S-NAr chemistry of the commercially available pentafluorophenylalanine Boc-Z. These novel unnatural amino acids display distinct F-19 NMR signatures, making them powerful tools for analyzing protein-membrane interactions with NMR spectroscopy.

引用

页码：528 / 531

页数：4

共 33 条

[1]

BAYLEY H, 1978, TETRAHEDRON LETT, P3633

[2] Marfey's reagent for chiral amino acid analysis:: A review [J].

Bhushan, R ;

Brückner, H .

AMINO ACIDS, 2004, 27 (3-4) :231-247

[3] De novo design of defined helical bundles in membrane environments [J].

Bilgiçer, B ;

Kumar, K .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (43) :15324-15329

[4] Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores [J].

Bilgiçer, B ;

Xing, X ;

Kumar, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11815-11816

[5] A coiled coil with a fluorous core [J].

Bilgiçer, B ;

Fichera, A ;

Kumar, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4393-4399

[6] 19F NMR applications in chemical biology [J].

Cobb, Steven L. ;

Murphy, Cormac D. .

JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (02) :132-143

[7] Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences [J].

Coin, Irene ;

Beyermann, Michael ;

Bienert, Michael .

NATURE PROTOCOLS, 2007, 2 (12) :3247-3256

[8] SANDMEYER AND RELATED REACTIONS [J].

COWDREY, WA ;

DAVIES, DS .

QUARTERLY REVIEWS, 1952, 6 (04) :358-379

[9] Aromatic allylation via diazotization: Variation of the allylic moiety and a short route to a benzazepine derivative [J].

Ek, F ;

Wistrand, LG ;

Frejd, T .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1911-1918

[10] 19F NMR studies of solvent exposure and peptide binding to an SH3 domain [J].

Evanics, Ferenc ;

Kitevski, Julianne L. ;

Bezsonova, Irina ;

Forman-Kay, Julie ;

Prosser, R. Scott .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2007, 1770 (02) :221-230

← 1 2 3 4 →