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In our study on the isolation and structure elucidation of biologically active compounds from marine invertebrates, we synthesized the four diastereomers of C_<16>-phytosphingosine (10, 12, 25, and 26), acanthacerebroside A (1), and D-galactosylceramide (3b) as described below. (2S, 3S)-Allylic alcohol, which was prepared from the L-serine derivative and the (E)-vinylalane compound, was converted into (2S, 3S, 4R)- and (2S, 3S, 4S)-phytosphingosines by epoxidation, DIBAH reduction, and debenzylation. The same treatment of (2S, 3R)-allylic alcohol gave (2S, 3R, 4R)- and (2S, 3R, 4S)-phytosphingosines. (2R)-Acetoxytetracosanoic acid was prepared and coupled to (2S, 3S, 4R)-phytosphingosine to give the ceramide (34). Glycosylation of 34 gave the desired monoglycoside (36) and the bisglycoside (37). 36 was converted into 1 by deacetylation. New D-galactosylceramides were isolated from Chondropsis sp., but the absolute stereochemistry has not been determined. Therefore, (2S, 3S, 4R, 6E)- and (2R, 3R, 4R, 6E)-phytosphingosines were prepared via asymmetric epoxidation. The former was transformed to (2S, 3S, 4R, 6E, 2'R)-D-galactosylceramide and its heptaacetate. The spectral data of them were in excellent agreement with those of the natural specimens.

2018-06-01 05:16:36
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1 0 0 0 OA 新規物綴込

出版者: 写
巻号頁・発行日: vol.[2],

2018-06-01 05:00:06
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1 0 0 0 OA Synthesis of a New Cerebroside from a Chondropsis sp. Sponge

著者: 本田昌徳上田義隆杉山重夫古森徹哉
出版者: The Pharmaceutical Society of Japan
雑誌: Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日: vol.39, no.6, pp.1385-1391, 1991-06-25 (Released:2008-03-31)
参考文献数: 24
被引用文献数: 12 20

A cerebroside, 1-O-(β-D-galactopyranosyloxy)-(2S, 3S, 4R, 6E)-2-[(R)-2-hydroxytetracosanoylamino]-17-methyl-6-octadecene-3, 4-diol (2), was asymmetrically synthesized from isobutyraldehyde. On the basis of a comparison of the physical data, the absolute structure of a new cerebroside 1b from a Chondropsis sp. sponge is thought to be the same at that of 2.

2018-06-01 04:57:09
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1 0 0 0 OA 韓国ソウルのニュータウン

著者: 岩鼻通明
出版者: The Tohoku Geographical Association
雑誌: 季刊地理学 (ISSN:09167889)
巻号頁・発行日: vol.47, no.1, pp.46-48, 1995-03-15 (Released:2010-04-30)
参考文献数: 2

2018-06-01 04:53:38
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1 0 0 0 靖国戦後秘史 : A級戦犯を合祀した男

著者: 毎日新聞「靖国」取材班 [著]
出版者: KADOKAWA
巻号頁・発行日: 2015

2018-06-01 03:55:02
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https://ci.nii.ac.jp/ncid/BB19761400

1 0 0 0 気孔のパターン形成と分化--細胞間シグナル伝達機構の新知見

1 0 0 0 植物のメリステム:植物の形づくりを担う細胞集団における細胞間コミュニケ-ション

1 0 0 0 JAPANESE AUTHOR 葉の気孔から発生の謎を解く

1 0 0 0 気孔の発生--コミュニケーション、細胞運命と決定

1 0 0 0 植物の形を調節するペプチドホルモン

1 0 0 0 Front Runner 挑む(第55回)鳥居啓子 米ワシントン大学(シアトル)教授 名古屋大学トランスフォーマティブ生命分子研究所客員教授 植物の気孔から発生の謎に迫る

1 0 0 0 OA Cell differentiation of the outermost cells of developing endosperm in carrot

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1 0 0 0 OA 笑府衿裂米

1 0 0 0 Purification and molecular cloning of epiregulin, a novel member of epidermal growth factor family

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1 0 0 0 カテコールアミン関連物質および酵素のルミネッセンスによる測定

1 0 0 0 カルボン酸エステル加水分解酵素活性測定のための新しい発色基質の開発

1 0 0 0 ヒト化抗体医薬品の体内動態に関する研究 : 抗ヒトInterleukin-6受容体抗体Tocilizumabと抗HM1.24抗体AHMの体内動態に関する比較研究

1 0 0 0 OA 取箇帳 10巻

1 0 0 0 4 Acanthacerebroside A並びに関連海産スフィンゴ糖脂質の立体化学(口頭発表の部)

1 0 0 0 OA 新規物綴込

1 0 0 0 OA Synthesis of a New Cerebroside from a Chondropsis sp. Sponge

1 0 0 0 OA 韓国ソウルのニュータウン

1 0 0 0 靖国戦後秘史 : A級戦犯を合祀した男

1 0 0 0 Front Runner 挑む(第55回)鳥居啓子米ワシントン大学(シアトル)教授名古屋大学トランスフォーマティブ生命分子研究所客員教授植物の気孔から発生の謎に迫る