Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols

Takeshi Nagasaki, Onari Kimura, Masakatsu Ukon, Susumu Arimori, Itaru Hamachi, Seiji Shinkai

Research output: Contribution to journalArticle

78 Citations (Scopus)

Abstract

The first dendritic crown ether polymers ('crowned' arborols: G1, G2 and G3) have been synthesized and characterized. The convergent synthetic method was found to be more convenient than the divergent synthetic method. The building block in the branch was prepared from N-benzyloxycarbonyl-1,4,10,13-tetraoxa-7, 16-diazacyclooctadecane and 3,5-bis(ethoxycarbonylmethoxy)benzoyl chloride. Since the basic repeating unit is the amino dicarboxylic acid, one can utilize the methods developed for peptide synthesis. Final products were obtained in moderate yields by coupling of each generational fragment with a core (benzene-1,3,5-tricarbonyl trichloride) followed by reduction of all amide linkages to tertiary amine linkages by borane-dimethyl sulfide. The complexation ability of these 'crowned' arborols was estimated by two-phase solvent extraction of alkali picrate salts. We found that some of these arborols can solubilize proteins in organic solvents.

Original languageEnglish
Pages (from-to)75-81
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number1
Publication statusPublished - Dec 1 1994

Fingerprint

Dicarboxylic Amino Acids
Boranes
Crown Ethers
Alkalies
Solvent extraction
Complexation
Amides
Organic solvents
Amines
Polymers
Salts
Metals
Peptides
Proteins
1,3,5-benzene-tricarbonyl trichloride
picric acid
benzoyl chloride
dimethyl sulfide

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Nagasaki, T., Kimura, O., Ukon, M., Arimori, S., Hamachi, I., & Shinkai, S. (1994). Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols. Journal of the Chemical Society, Perkin Transactions 1, (1), 75-81.

Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols. / Nagasaki, Takeshi; Kimura, Onari; Ukon, Masakatsu; Arimori, Susumu; Hamachi, Itaru; Shinkai, Seiji.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 1, 01.12.1994, p. 75-81.

Research output: Contribution to journalArticle

Nagasaki, T, Kimura, O, Ukon, M, Arimori, S, Hamachi, I & Shinkai, S 1994, 'Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols', Journal of the Chemical Society, Perkin Transactions 1, no. 1, pp. 75-81.
Nagasaki, Takeshi ; Kimura, Onari ; Ukon, Masakatsu ; Arimori, Susumu ; Hamachi, Itaru ; Shinkai, Seiji. / Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols. In: Journal of the Chemical Society, Perkin Transactions 1. 1994 ; No. 1. pp. 75-81.
@article{92e91eaf4c304f94b79586a6480468ac,
title = "Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols",
abstract = "The first dendritic crown ether polymers ('crowned' arborols: G1, G2 and G3) have been synthesized and characterized. The convergent synthetic method was found to be more convenient than the divergent synthetic method. The building block in the branch was prepared from N-benzyloxycarbonyl-1,4,10,13-tetraoxa-7, 16-diazacyclooctadecane and 3,5-bis(ethoxycarbonylmethoxy)benzoyl chloride. Since the basic repeating unit is the amino dicarboxylic acid, one can utilize the methods developed for peptide synthesis. Final products were obtained in moderate yields by coupling of each generational fragment with a core (benzene-1,3,5-tricarbonyl trichloride) followed by reduction of all amide linkages to tertiary amine linkages by borane-dimethyl sulfide. The complexation ability of these 'crowned' arborols was estimated by two-phase solvent extraction of alkali picrate salts. We found that some of these arborols can solubilize proteins in organic solvents.",
author = "Takeshi Nagasaki and Onari Kimura and Masakatsu Ukon and Susumu Arimori and Itaru Hamachi and Seiji Shinkai",
year = "1994",
month = "12",
day = "1",
language = "English",
pages = "75--81",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1472-7781",
publisher = "Chemical Society",
number = "1",

}

TY - JOUR

T1 - Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols

AU - Nagasaki, Takeshi

AU - Kimura, Onari

AU - Ukon, Masakatsu

AU - Arimori, Susumu

AU - Hamachi, Itaru

AU - Shinkai, Seiji

PY - 1994/12/1

Y1 - 1994/12/1

N2 - The first dendritic crown ether polymers ('crowned' arborols: G1, G2 and G3) have been synthesized and characterized. The convergent synthetic method was found to be more convenient than the divergent synthetic method. The building block in the branch was prepared from N-benzyloxycarbonyl-1,4,10,13-tetraoxa-7, 16-diazacyclooctadecane and 3,5-bis(ethoxycarbonylmethoxy)benzoyl chloride. Since the basic repeating unit is the amino dicarboxylic acid, one can utilize the methods developed for peptide synthesis. Final products were obtained in moderate yields by coupling of each generational fragment with a core (benzene-1,3,5-tricarbonyl trichloride) followed by reduction of all amide linkages to tertiary amine linkages by borane-dimethyl sulfide. The complexation ability of these 'crowned' arborols was estimated by two-phase solvent extraction of alkali picrate salts. We found that some of these arborols can solubilize proteins in organic solvents.

AB - The first dendritic crown ether polymers ('crowned' arborols: G1, G2 and G3) have been synthesized and characterized. The convergent synthetic method was found to be more convenient than the divergent synthetic method. The building block in the branch was prepared from N-benzyloxycarbonyl-1,4,10,13-tetraoxa-7, 16-diazacyclooctadecane and 3,5-bis(ethoxycarbonylmethoxy)benzoyl chloride. Since the basic repeating unit is the amino dicarboxylic acid, one can utilize the methods developed for peptide synthesis. Final products were obtained in moderate yields by coupling of each generational fragment with a core (benzene-1,3,5-tricarbonyl trichloride) followed by reduction of all amide linkages to tertiary amine linkages by borane-dimethyl sulfide. The complexation ability of these 'crowned' arborols was estimated by two-phase solvent extraction of alkali picrate salts. We found that some of these arborols can solubilize proteins in organic solvents.

UR - http://www.scopus.com/inward/record.url?scp=37049081931&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049081931&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:37049081931

SP - 75

EP - 81

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1472-7781

IS - 1

ER -