A branched, hydrogen-bonded heterodimer: a novel system for achieving high stability and specificity

Jason B. Bialecki; Li Hua Yuan; Bing Gong

doi:10.1016/j.tet.2007.04.043

A branched, hydrogen-bonded heterodimer: a novel system for achieving high stability and specificity

Jason B. Bialecki
, Li Hua Yuan
, Bing Gong

Chemistry

SUNY Buffalo

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Presented is a description of the design, synthesis, and characterization of a novel, branched, six hydrogen-bonded heterodimer termed 'trident'. Two branched oligoamide molecules, 1 and 2, with complementary hydrogen-bonding sequences 3(AD) and 3(DA), respectively, were found to form a very stable (K_a≥9×10⁶ M^-1) heterodimer in chloroform. Confirmation of the high stability of the heterodimer was obtained through 1D and 2D ¹H NMR spectroscopy, thin-layer chromatography (TLC), and vapor pressure osmometry (VPO). The stability of the trident occurs through the cooperative action of six programmed hydrogen-bonding interactions, which are facilitated by the pre-organization of the individual strands through intramolecular hydrogen bonding.

Original language	English
Pages (from-to)	5460-5469
Number of pages	10
Journal	Tetrahedron
Volume	63
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2007.04.043
State	Published - Jun 18 2007

Keywords

Heterodimer
Hydrogen-bonding
NMR
Oligoamide
Self-assembly

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10.1016/j.tet.2007.04.043

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title = "A branched, hydrogen-bonded heterodimer: a novel system for achieving high stability and specificity",

abstract = "Presented is a description of the design, synthesis, and characterization of a novel, branched, six hydrogen-bonded heterodimer termed 'trident'. Two branched oligoamide molecules, 1 and 2, with complementary hydrogen-bonding sequences 3(AD) and 3(DA), respectively, were found to form a very stable (Ka≥9×106 M-1) heterodimer in chloroform. Confirmation of the high stability of the heterodimer was obtained through 1D and 2D 1H NMR spectroscopy, thin-layer chromatography (TLC), and vapor pressure osmometry (VPO). The stability of the trident occurs through the cooperative action of six programmed hydrogen-bonding interactions, which are facilitated by the pre-organization of the individual strands through intramolecular hydrogen bonding.",

keywords = "Heterodimer, Hydrogen-bonding, NMR, Oligoamide, Self-assembly",

author = "Bialecki, \{Jason B.\} and Yuan, \{Li Hua\} and Bing Gong",

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doi = "10.1016/j.tet.2007.04.043",

language = "English",

volume = "63",

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journal = "Tetrahedron",

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TY - JOUR

T1 - A branched, hydrogen-bonded heterodimer

T2 - a novel system for achieving high stability and specificity

AU - Bialecki, Jason B.

AU - Yuan, Li Hua

AU - Gong, Bing

PY - 2007/6/18

Y1 - 2007/6/18

N2 - Presented is a description of the design, synthesis, and characterization of a novel, branched, six hydrogen-bonded heterodimer termed 'trident'. Two branched oligoamide molecules, 1 and 2, with complementary hydrogen-bonding sequences 3(AD) and 3(DA), respectively, were found to form a very stable (Ka≥9×106 M-1) heterodimer in chloroform. Confirmation of the high stability of the heterodimer was obtained through 1D and 2D 1H NMR spectroscopy, thin-layer chromatography (TLC), and vapor pressure osmometry (VPO). The stability of the trident occurs through the cooperative action of six programmed hydrogen-bonding interactions, which are facilitated by the pre-organization of the individual strands through intramolecular hydrogen bonding.

AB - Presented is a description of the design, synthesis, and characterization of a novel, branched, six hydrogen-bonded heterodimer termed 'trident'. Two branched oligoamide molecules, 1 and 2, with complementary hydrogen-bonding sequences 3(AD) and 3(DA), respectively, were found to form a very stable (Ka≥9×106 M-1) heterodimer in chloroform. Confirmation of the high stability of the heterodimer was obtained through 1D and 2D 1H NMR spectroscopy, thin-layer chromatography (TLC), and vapor pressure osmometry (VPO). The stability of the trident occurs through the cooperative action of six programmed hydrogen-bonding interactions, which are facilitated by the pre-organization of the individual strands through intramolecular hydrogen bonding.

KW - Heterodimer

KW - Hydrogen-bonding

KW - NMR

KW - Oligoamide

KW - Self-assembly

UR - https://www.scopus.com/pages/publications/34248579511

U2 - 10.1016/j.tet.2007.04.043

DO - 10.1016/j.tet.2007.04.043

M3 - Article

AN - SCOPUS:34248579511

SN - 0040-4020

VL - 63

SP - 5460

EP - 5469

JO - Tetrahedron

JF - Tetrahedron

IS - 25

ER -

A branched, hydrogen-bonded heterodimer: a novel system for achieving high stability and specificity

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Keywords

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