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

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Fältnamn	Indikatorer	Metadata
000		03370naa a2200445 4500
001		oai:DiVA.org:kth-187297
003		SwePub
008		160519s2016 \| \|\|\|\|\|\|\|\|\|\|\|000 \|\|eng\|
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-1872972 URI
024	7	a https://doi.org/10.3390/molecules210303662 DOI
040		a (SwePub)kth
041		a engb eng
042		9 SwePub
072	7	a ref2 swepub-contenttype
072	7	a art2 swepub-publicationtype
100	1	a Stenström, Patriku KTH,Ytbehandlingsteknik4 aut0 (Swepub:kth)u14if6dt
245	1 0	a Fluoride-promoted esterification (FPE) chemistry :b A robust route to Bis-MPA dendrons and their postfunctionalization
264		c 2016-03-17
264	1	b MDPI AG,c 2016
338		a print2 rdacarrier
500		a QC 20160519
520		a 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.
650	7	a NATURVETENSKAPx Kemix Polymerkemi0 (SwePub)104062 hsv//swe
650	7	a NATURAL SCIENCESx Chemical Sciencesx Polymer Chemistry0 (SwePub)104062 hsv//eng
653		a Biotin
653		a Bis-MPA
653		a Carbonyl diimidazole
653		a CuAAC click chemistry
653		a Dendritic polymers
653		a Dendron
653		a FPE chemistry
653		a Polyesters
700	1	a Andrén, Oliver C. J.u KTH,Fiber- och polymerteknologi4 aut0 (Swepub:kth)u1fshusr
700	1	a Malkoch, Michaelu KTH,Ytbehandlingsteknik4 aut0 (Swepub:kth)u18z6ljf
710	2	a KTHb Ytbehandlingsteknik4 org
773	0	t Moleculesd : MDPI AGg 21:3q 21:3x 1431-5157x 1420-3049
856	4	u https://doi.org/10.3390/molecules21030366y Fulltext
856	4	u https://www.mdpi.com/1420-3049/21/3/366/pdf
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-187297
856	4 8	u https://doi.org/10.3390/molecules21030366

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Av författaren/redakt...: Stenström, Patri ...; Andrén, Oliver C ...; Malkoch, Michael

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NATURVETENSKAP: NATURVETENSKAP; och Kemi; och Polymerkemi

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