Self-Assembly of Fluorinated Sugar Amino Acid Derived α,γ-Cyclic Peptides into Transmembrane Anion Transport

被引：25

作者：

Burade, Sachin S. ^{[1
]}

Saha, Tanmoy ^{[2
]}

Bhuma, Naresh ^{[1
]}

Kumbhar, Navanath ^{[1
]}

Kotmale, Amol ^{[3
]}

Rajamohanan, Pattuparambil R. ^{[3
]}

Gonnade, Rajesh G. ^{[4
]}

Talukdar, Pinaki ^{[2
]}

Dhavale, Dilip D. ^{[1
]}

机构：

[1] Savitribai Phule Pune Univ, Garware Res Ctr, Dept Chem, Pune 411007, Maharashtra, India

[2] IISER, Pune 411008, Maharashtra, India

[3] CSIR NCL, Cent NMR Facil, Pune 411008, Maharashtra, India

[4] CSIR NCL, CMC, Pune 411008, Maharashtra, India

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 21期

关键词：

ION-TRANSPORT; CYCLIC HOMOOLIGOMERS; CHANNELS; NANOTUBES; NMR;

D O I：

10.1021/acs.orglett.7b02942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of fluorinated sugar amino acid derived alpha,gamma-cyclic tetra- and hexapeptides are reported. The IR, NMR, ESI-MS, CD, and molecular modeling studies of cyclic tetra- and hexapeptides showed C-2 and C-3 symmetric flat oval- and triangular-ring shaped, beta-strand conformations, respectively, which appear to self assemble into nanotubes. The alpha,gamma-cyclic hexapeptide (EC50 = 2.14 mu M) is found to be a more efficient ion transporter than alpha,gamma-cyclic tetrapeptide (EC50 = 14.75 mu M). The anion selectivity and recognition of alpha,gamma-cyclic hexapeptide with NO3- ion is investigated.

引用

页码：5948 / 5951

页数：4

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