Bioorganic Chemistry p. 51 - 60 (1998)
Update date:2022-07-29
Topics: Characterization Materials and Reagents Purification and Isolation Safety Functionalization of PEI Activation of TACD and β-cyclodextrin Conjugation of TACD to PEI Conjugation of β-cyclodextrin to PEI Proximity and Site-Directed Functionalization Testing and Optimization
Kim, Sung Min
Hong, In Seok
Suh, Junghun
A novel methodology for the site-directed introduction of a functional group in the vicinity of β-cyclodextrin (CD) on the backbone of branched poly(ethylenimine) (PEI) is developed. Site-directed or random attachment of 1,5,9-triazacyclododecane (TC) to CD-containing PEI followed by acetylation of the primary and secondary amines of the polymer backbone produced [TC- CD](SD)AcPEI or [TC-CD](Ran)AcPEI, respectively. By the addition of Ni(II), Cu(II), or Zn(II) ion, [M(II)TC-CD](SD)AcPEI or [M(II)TC-CD](Ran)AcPEI was obtained. The formation constant for the complexation of a hydrophobic ester revealed that the TC portion was indeed positioned in the vicinity of the CD cavity in [M(II)TC-CD](SD)AcPEI. Compared with [M(II)TC-CD](Ran)AcPEI, [M(II)TC-CD](SD)AcPEI appears to exert an extra stabilization effect (- ΔΔG°= 1.0-1.3 kcal/mol) on the complexed ester by hydrogen bonding between the metal-bound water of the polymer and the carbonyl group of the ester.
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Doi:10.1007/BF02290619
(1998)Doi:10.1021/jo9805394
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(1998)Doi:10.1021/jo981059f
(1998)