Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline

被引：9

作者：

Ulbrich, Dirk ^{[1
,2
]}

Daniliuc, Constantin G. ^{[1
]}

Haufe, Guenter ^{[1
,2
]}

机构：

[1] Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany

[2] Univ Munster, Cells In Mot Cluster Excellence, Waldeyerstr 15, D-48149 Munster, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 09期

关键词：

STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; FLUORINE; ENZYMES; BIOCATALYSIS; THIOETHERS; PEPTIDES; PROTEINS; DESIGN;

D O I：

10.1039/c6ob00131a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intending tosynthesize omega,omega-difluoroalkyl amino acid derivatives by oxidative desulfurization-fluorination reactions of suitable arylthio-2-phthalimido butanoates and pentanoates, in addition to small amounts of the target products, mainly alpha,omega-polyfluorinated amino acid derivatives were formed by additional sulfur-assisted alpha-fluorination. This novel structural motif was verified spectroscopically as well as by X-ray analysis. A plausible mechanism of formation is suggested. Using a different approach, delta, delta-difluoronorvaline hydrochloride was synthesized with at least 36% enantiomeric excess via deoxofluorination of the corresponding aldehyde.

引用

页码：2755 / 2767

页数：13

共 61 条

[1] Impact of fluorination on proteolytic stability of peptides: a case study with α-chymotrypsin and pepsin [J].

Asante, Vivian ;

Mortier, Jeremie ;

Wolber, Gerhard ;

Koksch, Beate .

AMINO ACIDS, 2014, 46 (12) :2733-2744

[2] Electrolytic partial fluorination of organic compounds.: Part 61:: The first example of direct α-fluorination of protected α-amino acids [J].

Baba, D ;

Fuchigami, T .

TETRAHEDRON LETTERS, 2002, 43 (27) :4805-4808

[3] Enhanced Refoldability and Thermoactivity of Fluorinated Phosphotriesterase [J].

Baker, Peter James ;

Montclare, Jin Kim .

CHEMBIOCHEM, 2011, 12 (12) :1845-1848

[4]

Banks R. E., 1994, ORGANOFLUORINE CHEM

[5]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine

[6] Evolution of fluorinated enzymes: An emerging trend for biocatalyst stabilization [J].

Biava, Hernan ;

Budisa, Nediljko .

ENGINEERING IN LIFE SCIENCES, 2014, 14 (04) :340-351

[7] SYNTHESIS AND STEREOCHEMISTRY OF 4 ISOMERIC PINANE-2,3-DIOLS [J].

CARLSON, RG ;

PIERCE, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (16) :2319-&

[8] Biocatalysis and enzymes in organic synthesis [J].

Davis, BG ;

Borer, V .

NATURAL PRODUCT REPORTS, 2001, 18 (06) :618-640

[9]

Dawson R. M. C., 1974, DATA BIOMEDICAL RES

[10]

Dmowski W., 2000, ORGANOFLUORINE COMPO

← 1 2 3 4 5 6 7 →