Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

Jenny Ågren; Johan Billing; Hans Grundberg; Ulf Nilsson

doi:10.1055/s-2006-942503

Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

Jenny Ågren, Johan Billing, Hans Grundberg, Ulf Nilsson

Centre for Analysis and Synthesis

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

Abstract

An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.

Original language	English
Pages (from-to)	3141-3145
Journal	Synthesis
Issue number	18
DOIs	https://doi.org/10.1055/s-2006-942503
Publication status	Published - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Free keywords

carbohydrates
macrocycles
cycloadditions
azides
amino acids

Access to Document

10.1055/s-2006-942503

Cite this

@article{8db778365f60470c8ebd4f7d8956f642,

title = "Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition",

abstract = "An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.",

keywords = "carbohydrates, macrocycles, cycloadditions, azides, amino acids",

author = "Jenny {\AA}gren and Johan Billing and Hans Grundberg and Ulf Nilsson",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

year = "2006",

doi = "10.1055/s-2006-942503",

language = "English",

pages = "3141--3145",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Oxford Polytechnic, Oxford",

number = "18",

}

TY - JOUR

T1 - Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

AU - Ågren, Jenny

AU - Billing, Johan

AU - Grundberg, Hans

AU - Nilsson, Ulf

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2006

Y1 - 2006

N2 - An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.

AB - An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.

KW - carbohydrates

KW - macrocycles

KW - cycloadditions

KW - azides

KW - amino acids

U2 - 10.1055/s-2006-942503

DO - 10.1055/s-2006-942503

M3 - Article

SN - 0039-7881

SP - 3141

EP - 3145

JO - Synthesis

JF - Synthesis

IS - 18

ER -

Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

Access to Document

Fingerprint

Cite this