2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation

被引：33

作者：

Gimenez, Diana ^{[1
]}

Dose, Anica ^{[1
]}

Robson, Nicholas L. ^{[1
]}

Sandford, Graham ^{[1
]}

Cobb, Steven L. ^{[1
]}

Coxon, Christopher R. ^{[2
]}

机构：

[1] Univ Durham, Dept Chem, South Rd, Durham DH1 3LE, England

[2] Liverpool John Moores Univ, Sch Pharm & Biomol Sci, Byrom St Campus, Liverpool L3 3AF, Merseyside, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 19期

基金：

英国工程与自然科学研究理事会;

关键词：

TRIFLUOROETHANOL; MIXTURES; ACID; PENTAFLUOROPYRIDINE; MACROCYCLIZATION; POLYPEPTIDES; SUBSTITUTION; DERIVATIVES; MECHANISM; WATER;

D O I：

10.1039/c7ob00295e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The SNAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both F-19-NMR analysis and further chemical modification. However, chemo-selective arylation in peptides containing multiple nucleophilic side chains currently presents a challenge to the field. Herein, we demonstrate that employing 2,2,2-trifluoroethanol (TFE) as a solvent in peptide SNAr reactions significantly improves nucleophile-selectivity when compared to N, N'-dimethylformamide (DMF).

引用

收藏

页码：4081 / 4085

页数：5

相关论文

共 30 条

[1] Solvent effects and mechanism for a nucleophilic aromatic substitution from QM/MM simulations [J].

Acevedo, O ;

Jorgensen, WL .

ORGANIC LETTERS, 2004, 6 (17) :2881-2884

[2] ACID IONIZATION CONSTANTS OF ALCOHOLS .1. TRIFLUOROETHANOL IN THE SOLVENTS H2O AND D2O [J].

BALLINGER, P ;

LONG, FA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (05) :1050-1053

[3] HETEROCYCLIC POLYFLUORO-COMPOUNDS .4. NUCLEOPHILIC SUBSTITUTION IN PENTAFLUOROPYRIDINE - PREPARATION AND PROPERTIES OF SOME 4-SUBSTITUTED 2,3,5,6-TETRAFLUOROPYRIDINES [J].

BANKS, RE ;

BURGESS, JE ;

CHENG, WM ;

HASZELDINE, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :575-+

[4] Unveiling the "booster effect" of fluorinated alcohol solvents:: Aggregation-induced conformational changes and cooperatively enhanced H-bonding [J].

Berkessel, Albrecht ;

Adrio, Jens A. ;

Huettenhain, Daniel ;

Neudoerfl, Jorg M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8421-8426

[5] The preparation and properties of polyfluoro aromatic and heteroaromatic compounds [J].

Brooke, GM .

JOURNAL OF FLUORINE CHEMISTRY, 1997, 86 (01) :1-76

[6] Trifluoroacetic Acid in 2,2,2-Trifluoroethanol Facilitates SNAr Reactions of Heterocycles with Arylamines [J].

Carbain, Benoit ;

Coxon, Christopher R. ;

Lebraud, Honorine ;

Elliott, Kristopher J. ;

Matheson, Christopher J. ;

Meschini, Elisa ;

Roberts, Amy R. ;

Turner, David M. ;

Wong, Christopher ;

Cano, Celine ;

Griffin, Roger J. ;

Hardcastle, Ian R. ;

Golding, Bernard T. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (08) :2311-2317

[7] Macrocycles from polyfluoro-pyridine derivatives [J].

Chambers, RD ;

Hoskin, PR ;

Khalil, A ;

Richmond, P ;

Sandford, G ;

Yufit, DS ;

Howard, JAK .

JOURNAL OF FLUORINE CHEMISTRY, 2002, 116 (01) :19-22

[8] Properties of 2,2,2-trifluoroethallol and water mixtures [J].

Chitra, R ;

Smith, PE .

JOURNAL OF CHEMICAL PHYSICS, 2001, 114 (01) :426-435

[9]

Gast K, 1999, PROTEIN SCI, V8, P625

[10] The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems [J].

Gimenez, Diana ;

Mooney, Caitlin A. ;

Dose, Anica ;

Sandford, Graham ;

Coxon, Christopher R. ;

Cobb, Steven L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (19) :4086-4095