N-chloroacyl-6-O-triphenylmethylchitosans: Useful intermediates for synthetic modifications of chitosan

Jukka Holappa; Tapio Nevalainen; Pasi Soininen; Matti Elomaa; Rustam Safin; Már Másson; Tomi Järvinen

doi:10.1021/bm049372g

N-chloroacyl-6-O-triphenylmethylchitosans: Useful intermediates for synthetic modifications of chitosan

Jukka Holappa^*, Tapio Nevalainen, Pasi Soininen, Matti Elomaa, Rustam Safin, Már Másson, Tomi Järvinen

^*Corresponding author for this work

Faculty of Pharmaceutical Sciences

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

39 Citations (Scopus)

Abstract

An efficient synthetic route was developed for the mild chloroacylation of chitosan with different chloroacyl chlorides. Full N-chloroacylation was obtained with this procedure without any O-acylation, and products having lower degrees of substitution can also be produced. Organo-soluble 6-O-triphenylmethylchitosan was used as a starting material for the acylation reactions. The resulting N-chloroacyl-6-O-triphenylmethylchitosan intermediates were also organo-soluble, and characterized by FT-IR. N-Methylpiperazine, moieties were attached to make end products that were sufficiently soluble for characterization by NMR and also to prove that the present intermediates could be used for further modifications. The end products were fully characterized by ¹H NMR, ¹³C NMR, and 2D ¹H-¹³C heteronuclear single-quantum correlation NMR spectroscopy. The degrees of substitution were determined by ¹H NMR. Molecular weight determination by GPC-LS displayed a significant degradation of the polymer. The weight-average molar masses (M_w) of the end products ranged from 29.6 to 49.4 kDa, when the M_w of the starting material was 144.2 kDa.

Original language	English
Pages (from-to)	858-863
Number of pages	6
Journal	Biomacromolecules
Volume	6
Issue number	2
DOIs	https://doi.org/10.1021/bm049372g
Publication status	Published - Mar 2005

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title = "N-chloroacyl-6-O-triphenylmethylchitosans: Useful intermediates for synthetic modifications of chitosan",

abstract = "An efficient synthetic route was developed for the mild chloroacylation of chitosan with different chloroacyl chlorides. Full N-chloroacylation was obtained with this procedure without any O-acylation, and products having lower degrees of substitution can also be produced. Organo-soluble 6-O-triphenylmethylchitosan was used as a starting material for the acylation reactions. The resulting N-chloroacyl-6-O-triphenylmethylchitosan intermediates were also organo-soluble, and characterized by FT-IR. N-Methylpiperazine, moieties were attached to make end products that were sufficiently soluble for characterization by NMR and also to prove that the present intermediates could be used for further modifications. The end products were fully characterized by 1H NMR, 13C NMR, and 2D 1H-13C heteronuclear single-quantum correlation NMR spectroscopy. The degrees of substitution were determined by 1H NMR. Molecular weight determination by GPC-LS displayed a significant degradation of the polymer. The weight-average molar masses (Mw) of the end products ranged from 29.6 to 49.4 kDa, when the Mw of the starting material was 144.2 kDa.",

author = "Jukka Holappa and Tapio Nevalainen and Pasi Soininen and Matti Elomaa and Rustam Safin and M{\'a}r M{\'a}sson and Tomi J{\"a}rvinen",

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doi = "10.1021/bm049372g",

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T2 - Useful intermediates for synthetic modifications of chitosan

AU - Holappa, Jukka

AU - Nevalainen, Tapio

AU - Soininen, Pasi

AU - Elomaa, Matti

AU - Safin, Rustam

AU - Másson, Már

AU - Järvinen, Tomi

PY - 2005/3

Y1 - 2005/3

N2 - An efficient synthetic route was developed for the mild chloroacylation of chitosan with different chloroacyl chlorides. Full N-chloroacylation was obtained with this procedure without any O-acylation, and products having lower degrees of substitution can also be produced. Organo-soluble 6-O-triphenylmethylchitosan was used as a starting material for the acylation reactions. The resulting N-chloroacyl-6-O-triphenylmethylchitosan intermediates were also organo-soluble, and characterized by FT-IR. N-Methylpiperazine, moieties were attached to make end products that were sufficiently soluble for characterization by NMR and also to prove that the present intermediates could be used for further modifications. The end products were fully characterized by 1H NMR, 13C NMR, and 2D 1H-13C heteronuclear single-quantum correlation NMR spectroscopy. The degrees of substitution were determined by 1H NMR. Molecular weight determination by GPC-LS displayed a significant degradation of the polymer. The weight-average molar masses (Mw) of the end products ranged from 29.6 to 49.4 kDa, when the Mw of the starting material was 144.2 kDa.

AB - An efficient synthetic route was developed for the mild chloroacylation of chitosan with different chloroacyl chlorides. Full N-chloroacylation was obtained with this procedure without any O-acylation, and products having lower degrees of substitution can also be produced. Organo-soluble 6-O-triphenylmethylchitosan was used as a starting material for the acylation reactions. The resulting N-chloroacyl-6-O-triphenylmethylchitosan intermediates were also organo-soluble, and characterized by FT-IR. N-Methylpiperazine, moieties were attached to make end products that were sufficiently soluble for characterization by NMR and also to prove that the present intermediates could be used for further modifications. The end products were fully characterized by 1H NMR, 13C NMR, and 2D 1H-13C heteronuclear single-quantum correlation NMR spectroscopy. The degrees of substitution were determined by 1H NMR. Molecular weight determination by GPC-LS displayed a significant degradation of the polymer. The weight-average molar masses (Mw) of the end products ranged from 29.6 to 49.4 kDa, when the Mw of the starting material was 144.2 kDa.

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N-chloroacyl-6-O-triphenylmethylchitosans: Useful intermediates for synthetic modifications of chitosan

Abstract

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