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2 protocols using mannose

1

Synthesis of Cholesterol-Based Lipid Conjugates

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Cholesteryl (3-((2-hydroxyethyl)amino)propyl)carbamate hydroiodide (HAPC-Chol) was synthesized as described previously (13 (link)). N-(2-(2-Hydroxyethylamino)ethyl)cholesteryl- 3-carboxamide (OH-Chol) and cholesteryl (2-((2-hydroxyethyl)amino)ethyl)carbamate (OH-C-Chol) were synthesized as described previously (14 (link)). 1,2-Dioleoyl- 3- trimethylammonium-propane methyl sulfate salt (DOTAP) was obtained from Avanti Polar Lipids Inc. Dimethyldioctadecylammonium bromide (DDAB, product name: DC-1-18) and 11- ((1,3- bis(dodecanoyloxy)- 2- ((dodecanoyloxy)methyl)propan- 2- yl) amino)- N,N,N- trimethyl-11- oxoundecan-1- aminium bromide (product name: TC-1-12) were obtained from Sogo Pharmaceutical Co., Ltd.. 1,2-Dioleoyl- sn- glycero- 3-phosphoethanolamine (DOPE, COATSOME ME-8181) was obtained from NOF Co., Ltd.. Glucose, fructose, galactose, mannose, sucrose, trehalose dihydrate, maltose monohydrate, lactose monohydrate, lactulose, cellobiose, and raffinose pentahydrate were obtained from Wako Pure Chemical Industries, Ltd.. Melezitose was purchased form Sigma-Aldrich Co. LLC. All other chemicals were of the highest grade available.
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2

Structural Relaxation of Hemicellulose for Delignification

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Cellulose, monosaccharides
(glucose, xylose, arabinose, galactose, mannose), lower organic acids,
NaOH, and Na2CO3 were purchased from Wako Pure
Chemical Industries. A type of xylan, derived from beech wood, was
purchased from SERVA Electrophoresis. Ultrapurified water with an
electrical resistance of over 18.2 MΩ was prepared with a Milli-Q
water purification system (Merck, MPGP02001). Japanese cedar in the
form of particles sized 0.85–2 mm was used as the starting
material. It was subjected to a steam pretreatment at 220 °C
under atmospheric pressure. This pretreatment was performed to cause
structural relaxation of hemiCellulose and thereby promote the delignification.33 (link) The procedure of the pretreatment is described
in detail in the Supporting Information. The compositions of the original and pretreated cedars are listed
in Table 3.
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