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5 protocols using acetic anhydride

1

Synthesis of Amine-Functionalized Aromatic Polyimides

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From Kanto Chemical Co., Inc., 3-nitrophthalic anhydride, 3-nitrophthalic acid, and acetic anhydride were purchased and used as received. Trifluoroacetic anhydride, cyclohexylamine and Pd/C (55% water) were purchased from Tokyo Kasei Co., Ltd. and were used as received. In addition, 4,4ʹ-oxydiphthalic dianhydride (ODPA), purchased from MANAC Inc., was sublimed under reduced pressure. DCHM and trans-1,4-cyclohxanediamine (tDACH), purchased from Tokyo Kasei Co., Ltd., were purified by recrystallization from n-hexane and subsequent sublimation under reduced pressure. N,O-bis(trimethylsilyl) trifluoroacetamide (BSTFA, ≥99%) and N,N-dimethylacetamide (DMAc, anhydrous) were purchased from Sigma-Aldrich and used as received.
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2

Cellulose Milling and Acetylation Protocol

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Cellulose (ARBOCEL 600)
was obtained from J. Rettenmaier & Söhne GMBH + Co. KG
(Rosenberg, Germany). LC was prepared by milling at 10 °C with
a rotation speed of 180 rpm with a shear and cooling milling machine
based on KGW-G015 (West Co., Ltd., Japan), modified by Nishioka et al.(18 (link)) The radius of the mortars
was 45 mm. The clearance between upper and lower mortars was 10 μm.
The upper mortar was fixed and the lower mortar rotated around the
center. Samples were injected through a slot located on the upper
mortar. The distance between the slot and the center was 20 mm. The
samples were grinded in a region of mortars in the radial distance
between 20 and 45 mm. The injected samples were discharged out typically
in two to five rotations of the lower mortar after injection. Therefore,
the estimated processing time in the mill machine calculated from
the size of the mortar and the rotation speed is 1 or 2 s. Acetic
anhydride was purchased from Tokyo Kasei Kogyo (Tokyo, Japan). I2, acetic anhydride, Na2S2O3, ethanol, and ethyl acetate were purchased from Kanto Chemical (Tokyo,
Japan). All of the reagents were used as received.
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3

Quantification of Neuroactive Amino Acids

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Authentic compounds of GLYP, GLUF, and AMPA were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan); MPPA, (±)-2-amino-4-phosphonobutyric acid (AP-4), and DL-2-amino-5-phosphonopentanoic acid (AP-5) were purchased from Merck KGaA (Darmstadt, Germany); DL-2-amino-3-phosphonopropionic acid (APPA) was purchased from Tocris Bioscience (Minneapolis, MN, USA); stable isotope-labeled GLYP (GLYP13C215N) was purchased from LGC labor GmbH (Augsburg, Germany). The chemical structures of GLYP, GLUF, AMPA, MPPA, GLYP13C215N, AP-4, AP-5, and APPA are shown in Fig. 1A; the N-acetyl O-methyl derivatized compounds are shown in Fig. 1B. Acetic anhydride, ammonium formate, and acetonitrile were obtained from Kanto Chemical Co., Inc. (Tokyo, Japan); acetic acid was from Merck KGaA (Darmstadt, Germany); trimethyl orthoacetate was from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Blank human serum and urine samples were purchased from Cosmo Bio Co., Ltd. (Tokyo, Japan).
Stock solutions of the target analytes (100 ng/μL) and internal standard (IS) (50 ng/μL) were dissolved in 10% methanol and stored at –20°C.
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4

Enzymatic Synthesis of (Z)-3-Hexenol from Oyster

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CHIRAZYME L-2 and lipase PS were purchased from FUJIFILM Wako Pure Chemical Co. (Tokyo, Japan) . Oxone ® and vinylmagnesium bromide was purchased from Sigma-Aldrich Co. (Tokyo, Japan) . Acetic anhydride, pyridine and sodium borohydride were purchased from Kanto Chemical Co. (Tokyo, Japan) . 4-Dimethylaminopyridine and 2-iodobenzoic acid were purchased from Tokyo Chemical Industry Co. (Tokyo, Japan) . All other chemicals and solvents were commercially of the highest grade. (Z) -3-Hexenol, a geometrically pure form with ≧99%, was donated from Shiono Koryo Kaisha (Osaka, Japan) and Shiono Finess Co. (Osaka, Japan) .
The Pacific oyster Crassostrea gigas were purchased from an oyster farmer in Hiroshima Prefecture, Japan. The oysters were stored at -25℃ until use.
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5

Synthesis and Purification of Ionone and Ionol

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SanCat-R was purchased from FUJIFILM Wako Pure Chemical Co. (Tokyo, Japan) . β-and α-Ionones were purchased from Sigma-Aldrich Co. (Tokyo, Japan) . β-and α-Ionols were purified using silica gel column chromatography and/or distillation before use. Acetic anhydride, NaBH 4 and pyridine were purchased from Kanto Chemical Co. (Tokyo, Japan) . 4-Dimethylaminopyridine was purchased from Tokyo Chemical Industry Co. (Tokyo, Japan) . All other chemicals and solvents were commercially of the highest grade.
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