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

被引：26

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

共 34 条

[21] Circular dichroism spectroscopy of membrane proteins [J].

Miles, A. J. ;

Wallace, B. A. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (18) :4859-4872

[22] Antibacterial cyclic D,L-α-glycopeptides [J].

Motiei, Leila ;

Rahimipour, Shai ;

Thayer, Desiree A. ;

Wong, Chi-Huey ;

Ghadiri, M. Reza .

CHEMICAL COMMUNICATIONS, 2009, (25) :3693-3695

[23] Evidence of Nanotubular Self-Organization in Solution and Solid States of Heterochiral Cyclo 1:1 [α/α-Nα-Bn-hydrazino]mers Series [J].

Moussodia, Ralph-Olivier ;

Acherar, Samir ;

Romero, Eugenie ;

Didierjean, Claude ;

Jamart-Gregoire, Brigitte .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) :3022-3029

[24] Artificial beta-sheets [J].

Nowick, JS ;

Smith, EM ;

Pairish, M .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (06) :401-&

[25] Understanding organofluorine chemistry. An introduction to the C-F bond [J].

O'Hagan, David .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :308-319

[26] Designer hybrid cyclopeptides for membrane ion transport and tubular structures [J].

Ranganathan, D .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (11) :919-930

[27] Alkylated sugar amino acids:: A new entry toward highly functionalized dipeptide isosters [J].

Raunkjær, M ;

El Oualid, F ;

van der Marel, GA ;

Overkleeft, HS ;

Overhand, M .

ORGANIC LETTERS, 2004, 6 (18) :3167-3170

[28] Anion Recognition and Induced Self-Assembly of an ,-Cyclic Peptide To Form Spherical Clusters [J].

Rodriguez-Vazquez, Nuria ;

Amorin, Manuel ;

Alfonso, Ignacio ;

Granja, Juan R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) :4504-4508

[29]

ROWE SM, 2005, ENGL J MED, V352, P1992

[30] Chloride Transport through Supramolecular Barrel-Rosette Ion Channels: Lipophilic Control and Apoptosis-Inducing Activity [J].

Saha, Tanmoy ;

Gautam, Amitosh ;

Mukherjee, Arnab ;

Lahiri, Mayurika ;

Talukdar, Pinaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (50) :16443-16451

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