Application of Decafluorobiphenyl (DFBP) Moiety as a Linker in Bioconjugation

被引：7

作者：

Alapour, Saba ^{[1
]}

de la Torre, Beatriz G. ^{[2
]}

Ramjugernath, Deresh ^{[3
]}

Koorbanally, Neil A. ^{[1
]}

Albericio, Fernando ^{[1
,4
,5
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem & Phys, Private Bag X54001, ZA-4000 Durban, South Africa

[2] Univ KwaZulu Natal, KRISP, Coll Hlth Sci, ZA-4001 Durban, South Africa

[3] Univ KwaZulu Natal, Sch Chem Engn, ZA-4041 Durban, South Africa

[4] Univ Barcelona, CIBER BBN, Networking Ctr Bioengn Biomat & Nanomed, E-08028 Barcelona, Spain

[5] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

来源：

BIOCONJUGATE CHEMISTRY | 2018年 / 29卷 / 02期

基金：

新加坡国家研究基金会;

关键词：

FLUORINATED AMINO-ACIDS; F-19; NMR-SPECTROSCOPY; NITRIC-OXIDE SYNTHASE; C-F BOND; NUCLEOPHILIC-SUBSTITUTION; RHENIUM(I)-DIIMINE WIRES; UNPROTECTED PEPTIDES; CLICK CHEMISTRY; MACROCYCLIZATION; DERIVATIVES;

D O I：

10.1021/acs.bioconjchem.7b00800

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Considerable attention has been devoted to fluorinated compounds due to their unique and interesting properties. Many modern pharmaceuticals contain fluorinated substituents, which are commonly synthesized using selective fluorinating reagents. Decafluorobiphenyl (DFBP) as a fluorinated linker is susceptible to nucleophilic attack. This nucleophilic reaction has been widely studied using various nucleophiles. Sulfur and nitrogen containing nucleophiles have been of particular interest, especially in bioconjugated reactions. This review focuses on the SNAr reactivity of DFBP in formation of C-X (X = S, N) bonds, to be applied in bioconjugation in organic chemistry. The review aims to highlight the crucial factors that govern the chemistry behind the activation of F - C-Ar - C-Ar - F bonds as a linker in the synthesis of novel peptides, proteins, and biologics.

引用

页码：225 / 233

页数：9

共 65 条

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