Synthesis of an enantiomer of cellulose via cationic ring-opening polymerization

Yagura, Takahiro; Ikegami, Waki; Kamitakahara, Hiroshi; Takano, Toshiyuki

doi:10.1007/s10570-020-03512-z

Cited by 10 publications

(10 citation statements)

References 22 publications

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“…Cationic ring-opening copolymerization of glucose orthoester derivatives 2D and 2L Glucose orthoester derivatives 2D and 2L were synthesized from compounds 1D and 1L, respectively, according to previous reports (Adelwöhrer et al 2009, Yagura et al 2020). The ring-opening copolymerization of compounds 2D and 2L in a 1:1 ratio was conducted to give compound 3DL in quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

“…In the 1 H and 13 C NMR spectra, signals derived from C-1 and H-1 in pseudo-disaccharides with a D-D linkage have been reported to appear at different positions to those of C-1 and H-1 in pseudodisaccharides with a D-L linkage (Ogawa et al 1991, Duus et al 1994. The correlation signals derived from C-1/H-1 in compound 3D (D-D linkages) and an enantiomer of compound 3D (L-L linkages) have previously been reported to appear at the same position (Yagura et al 2020). In the NMR spectrum of compound 3DL, the correlation signal at 100.0/4.30 ppm was assigned to C-1/H-1 in the homochiral structure, while that at 99.3/4.72 ppm was assigned to C-1/H-1 in the heterochiral structure.…”

Section: Compound 3dlmentioning

confidence: 95%

“…Materials D-glucose (1D) and L-glucose (1L) were purchased from Nacalai Tesque Inc. (Kyoto, Japan) and Tokyo Chemical Industry Co. (Tokyo, Japan), respectively, and were dried in a vacuum desiccator under high vacuum (less than 1 hPa) at 70 C for 16 h before use. Compounds 2D and 2L were synthesized from compounds 1D and 1L, respectively, according to previous reports (Adelwöhrer et al 2009, Yagura et al 2020. Powdered 4 Å molecular sieves were activated in a GTO-2000 glass tube oven (Sibata Scientific Technology Ltd, Tokyo, Japan) Scheme 1.…”

Section: Methodsmentioning

confidence: 99%

“…This chirality is an important feature of high-value-added D-cellulose applications, such as chiral separation (Francotte 1994, Okamoto and Yashima 1998, D'Orazio et al 2018, Chankvetadze 2020, chiral nematic D-cellulose liquid crystals (Nishio et al 2016, Almedia et al 2018, and D-cellulose-based organocatalysts for asymmetric synthesis (Ikai et al 2011, Yasukawa et al 2015, Ranaivoarimanana et al 2019. Recently, an enantiomer of D-cellulose (denoted as Lcellulose hereafter) consisting of L-glucose was synthesized by our group using cationic ringopening polymerization (Yagura et al 2020). D-Cellulose and L-cellulose are crystalline and optically active polymers owing to their homochiral structures.…”

Section: Introductionmentioning

confidence: 99%

“…However, to our knowledge, D,L-cellulose has not been found in nature or synthesized artificially. Our group has already reported the syntheses of D-cellulose (Nakatsubo et al 1996, Adelwöhrer et al 2009) and L-cellulose (Yagura et al 2020) using cationic ring-opening polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of optically inactive cellulose via cationic ring-opening polymerization

et al. 2021

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Cellulose, which comprises D-glucose and L-glucose (D,L-cellulose), was synthesized from D-glucose (1D) and L-glucose (1L) via cationic ring-opening polymerization. Specifically, the ring-opening copolymerization of 3-O-benzyl-2,6-di-O-pivaloyl--D-glucopyranoside (2D) and 3-O-benzyl-2,6-di-O-pivaloyl-β-D-glucopyranoside (2L), synthesized from compounds 1D and 1L, respectively, in a 1:1 ratio, afforded 3-O-benzyl-2,6-di-O--D,L-glucopyranan (3DL) with a degree of polymerization (DPn) of 28.5 (Mw/Mn = 1.90) in quantitative yield.The deprotection of compound 3DL and subsequent acetylation proceeded smoothly to afford acetylated compound 4DL with a DPn of 18.6 (Mw/Mn = 2.08). The specific rotation of acetylated compound 4DL was +0.01, suggesting that acetylated compound 4DL was optically inactive cellulose triacetate. Furthermore, before acetylation, compound 4DL was an optically inactive cellulose comprising an almost racemic mixture of D-glucose and Lglucose. Compound 4DL was an amorphous polymer. This is the first reported synthesis of optically inactive D,L-cellulose.

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Section: Resultsmentioning

confidence: 99%

Section: Compound 3dlmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of optically inactive cellulose via cationic ring-opening polymerization

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2019–2020

Harvey

2023

Mass Spectrometry Reviews

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This review is the tenth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2020. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. The review is basically divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of arrays. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other areas such as medicine, industrial processes and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. The reported work shows increasing use of incorporation of new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented nearly 40 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show little sign of diminishing.

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The in vitro synthesis of cellulose – A mini-review

Lehrhofer

Goto

Kawada

et al. 2022

Carbohydrate Polymers

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Synthesis of an enantiomer of cellulose via cationic ring-opening polymerization

Cited by 10 publications

References 22 publications

Synthesis of optically inactive cellulose via cationic ring-opening polymerization

Synthesis of optically inactive cellulose via cationic ring-opening polymerization

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2019–2020

The in vitro synthesis of cellulose – A mini-review

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