Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure

Alexandra Bordes; Ana Poveda; Nathalie Fontelle; Ana Ardá; Jérôme Guillard; Yi Bin Ruan; Jérôme Marrot; Shuki Imaeda; Atsushi Kato; Jérôme Désiré; Juan Xie; Jesús Jiménez-Barbero; Yves Blériot

doi:10.1016/j.carres.2021.108258

Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure

Alexandra Bordes, Ana Poveda, Nathalie Fontelle, Ana Ardá, Jérôme Guillard, Yi Bin Ruan, Jérôme Marrot, Shuki Imaeda, Atsushi Kato, Jérôme Désiré, Juan Xie^*, Jesús Jiménez-Barbero^*, Yves Blériot^*

^*Corresponding author for this work

Hospital Pharmacy

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

3 Scopus citations

Abstract

Capitalizing on a recently reported iminosugar-based aza-crown (ISAC) accessed by a double Staudinger azaWittig coupling reaction, we have expanded the structural diversity of this new family of sweet cyclam analogs. Replacement of the two secondary amines linking the iminosugar units by two amide bonds obtained a cyclodimerization by with BOP and DIPEA led to a macrocycle that did not demonstrate efficient Zn²⁺ chelation unlike the parent ISAC. Introduction of two pyrene moieties on the secondary amines of the parent ISAC yielded a new fluoroionophore that selectively binds Hg²⁺ in methanol.

Original language	English
Article number	108258
Journal	Carbohydrate Research
Volume	501
DOIs	https://doi.org/10.1016/j.carres.2021.108258
State	Published - 2021/03

Keywords

Iminosugar
Ionophore
Macrocycle
NMR analysis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2021.108258

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Bordes, A., Poveda, A., Fontelle, N., Ardá, A., Guillard, J., Ruan, Y. B., Marrot, J., Imaeda, S., Kato, A., Désiré, J., Xie, J., Jiménez-Barbero, J., & Blériot, Y. (2021). Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure. Carbohydrate Research, 501, Article 108258. https://doi.org/10.1016/j.carres.2021.108258

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title = "Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure",

abstract = "Capitalizing on a recently reported iminosugar-based aza-crown (ISAC) accessed by a double Staudinger azaWittig coupling reaction, we have expanded the structural diversity of this new family of sweet cyclam analogs. Replacement of the two secondary amines linking the iminosugar units by two amide bonds obtained a cyclodimerization by with BOP and DIPEA led to a macrocycle that did not demonstrate efficient Zn2+ chelation unlike the parent ISAC. Introduction of two pyrene moieties on the secondary amines of the parent ISAC yielded a new fluoroionophore that selectively binds Hg2+ in methanol.",

keywords = "Iminosugar, Ionophore, Macrocycle, NMR analysis",

author = "Alexandra Bordes and Ana Poveda and Nathalie Fontelle and Ana Ard{\'a} and J{\'e}r{\^o}me Guillard and Ruan, {Yi Bin} and J{\'e}r{\^o}me Marrot and Shuki Imaeda and Atsushi Kato and J{\'e}r{\^o}me D{\'e}sir{\'e} and Juan Xie and Jes{\'u}s Jim{\'e}nez-Barbero and Yves Bl{\'e}riot",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = mar,

doi = "10.1016/j.carres.2021.108258",

language = "英語",

volume = "501",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure

AU - Bordes, Alexandra

AU - Poveda, Ana

AU - Fontelle, Nathalie

AU - Ardá, Ana

AU - Guillard, Jérôme

AU - Ruan, Yi Bin

AU - Marrot, Jérôme

AU - Imaeda, Shuki

AU - Kato, Atsushi

AU - Désiré, Jérôme

AU - Xie, Juan

AU - Jiménez-Barbero, Jesús

AU - Blériot, Yves

PY - 2021/3

Y1 - 2021/3

N2 - Capitalizing on a recently reported iminosugar-based aza-crown (ISAC) accessed by a double Staudinger azaWittig coupling reaction, we have expanded the structural diversity of this new family of sweet cyclam analogs. Replacement of the two secondary amines linking the iminosugar units by two amide bonds obtained a cyclodimerization by with BOP and DIPEA led to a macrocycle that did not demonstrate efficient Zn2+ chelation unlike the parent ISAC. Introduction of two pyrene moieties on the secondary amines of the parent ISAC yielded a new fluoroionophore that selectively binds Hg2+ in methanol.

AB - Capitalizing on a recently reported iminosugar-based aza-crown (ISAC) accessed by a double Staudinger azaWittig coupling reaction, we have expanded the structural diversity of this new family of sweet cyclam analogs. Replacement of the two secondary amines linking the iminosugar units by two amide bonds obtained a cyclodimerization by with BOP and DIPEA led to a macrocycle that did not demonstrate efficient Zn2+ chelation unlike the parent ISAC. Introduction of two pyrene moieties on the secondary amines of the parent ISAC yielded a new fluoroionophore that selectively binds Hg2+ in methanol.

KW - Iminosugar

KW - Ionophore

KW - Macrocycle

KW - NMR analysis

UR - http://www.scopus.com/inward/record.url?scp=85103114480&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2021.108258

DO - 10.1016/j.carres.2021.108258

M3 - 学術論文

C2 - 33618101

AN - SCOPUS:85103114480

SN - 0008-6215

VL - 501

JO - Carbohydrate Research

JF - Carbohydrate Research

M1 - 108258

ER -

Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure

Abstract

Keywords

ASJC Scopus subject areas

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