Fluoride-promoted esterification (FPE) chemistry: A robust route to Bis-MPA dendrons and their postfunctionalization

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Stenström, PatrikKTH,Ytbehandlingsteknik (author)

Fluoride-promoted esterification (FPE) chemistry : A robust route to Bis-MPA dendrons and their postfunctionalization

Article/chapterEnglish2016

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2016-03-17
MDPI AG,2016
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LIBRIS-ID:oai:DiVA.org:kth-187297
https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-187297URI
https://doi.org/10.3390/molecules21030366DOI

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Language:English
Summary in:English

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Subject category:ref swepub-contenttype
Subject category:art swepub-publicationtype

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QC 20160519
Bifunctional dendrons based on 2,2-bis(methylol)propionic acid (bis-MPA) are highly desirable scaffolds for biomedical applications. This is due to their flawless nature and large and exact number of functional groups as well as being biodegradable and biocompatible. Herein, we describe a facile divergent growth approach to their synthesis from monobenzylated tetraethylene glycol and post functionalization utilizing fluoride-promoted esterification (FPE) chemistry protocols. The scaffolds, presenting selectively deprotectable hydroxyls in the periphery and at the focal point, were isolated on a multigram scale with excellent purity up to the fourth generation dendron with a molecular weight of 2346 Da in seven reactions with a total yield of 50%. The third generation dendron was used as a model compound to demonstrate its functionalizability. Selective deprotection of the dendron's focal point was achieved with an outstanding yield of 94%, and biotin as well as azido functionalities were introduced to its focal point and periphery, respectively, through FPE chemistry. Bulky disperse red dyes were clicked through CuAAC to the dendron's azido groups, giving a biotinylated dendron with multivalent dyes with a molecular weight of 6252 Da in a total yield of 37% in five reactions with an average yield of 82% starting from the third generation focally and peripherally protected dendron. FPE chemistry proved to be a superb improvement over previous protocols towards bis-MPA dendrons as high purity and yields were obtained with less toxic solvents and greatly improved monomer utilization.

Subject headings and genre

NATURVETENSKAP Kemi Polymerkemi hsv//swe
NATURAL SCIENCES Chemical Sciences Polymer Chemistry hsv//eng
Biotin
Bis-MPA
Carbonyl diimidazole
CuAAC click chemistry
Dendritic polymers
Dendron
FPE chemistry
Polyesters

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Andrén, Oliver C. J.KTH,Fiber- och polymerteknologi(Swepub:kth)u1fshusr (author)
Malkoch, MichaelKTH,Ytbehandlingsteknik(Swepub:kth)u18z6ljf (author)
KTHYtbehandlingsteknik (creator_code:org_t)

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In:Molecules: MDPI AG21:31431-51571420-3049

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NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Polymer Chemistr ...

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By the university: Royal Institute of Technology

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