JP4726477B2 - 糖鎖合成におけるキャッピング試薬 - Google Patents
糖鎖合成におけるキャッピング試薬 Download PDFInfo
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- JP4726477B2 JP4726477B2 JP2004363017A JP2004363017A JP4726477B2 JP 4726477 B2 JP4726477 B2 JP 4726477B2 JP 2004363017 A JP2004363017 A JP 2004363017A JP 2004363017 A JP2004363017 A JP 2004363017A JP 4726477 B2 JP4726477 B2 JP 4726477B2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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Description
本発明では、糖鎖合成などにおける糖又はアルコールの水酸基のためのキャッピング試薬として、エチルイソシアナトホルメート又はエチルイソチオシアナトホルメートを使用する。
(1)短時間で水酸基と速やかに、かつ定量的に反応すること:
(2)中性条件で反応が進行し、反応条件が温和であること:
(3)グリコシル化反応、一時的な保護基の脱保護反応において完全に安定であること:
(4)グリコシル化反応、一時的な保護基の脱保護反応を妨げないこと:
(5)各種の一時的な保護基の脱保護条件下で安定であること:
が挙げられる。
原料とキャッピング剤の候補として考えられた試薬をジクロロメタン中において室温あるいは60℃にて撹拌した。原料の消失はTLC (thin layer chromatography) により確認した。反応液を濃縮後、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル混合系)により精製し、キャッピング体をそれぞれ得た。
試験例1で選択した4種の化合物について、ClAc基脱保護条件における耐性を検討した。具体的には、以下の通り行った。
data of 2; 1HNMR (CDCl3) δ 7.82-7.24 (m, 9H), 6.84-6.70 (m, 4H), 5.9
5 (m, 2H), 5.51 (s, 1H), 4.61 (t , 1H, J = 8.3 Hz), 4.40 (m, 1H), 4.07 (m, 2H), 3.90-3.86 (m, 3H), 3.68 (s, 3H), 1.23-1.14 (m, 4H);13C NMR (CDCl3) δ167.5 (C), 155.4 (C),150.1 (C), 150.0 (C), 149.3 (C), 136.3 (C), 134.1
(CH), 131.0 (C), 128.9 (CH), 127.9 (CH), 126.0 (CH), 123.6 (CH), 118.4 (CH), 114.3 (CH), 101.5 (CH), 97.8 (CH), 78.9 (CH), 71.2 (CH2), 68.3 (CH2), 66.1 (CH), 62.1 (CH2), 55.5 (CH3), 55.1 (CH), 14.2 (CH), 14.1 (CH).
= 10.9 Hz), 4.84-4.72 (m, 3H), 4.62-4.57 (dd, 2H), 4.51 (d, 1H, J = 3.4 Hz), 3.97 (t , 1H, J = 9.2 Hz), 3.73 (dd, 1H, J = 2.7, J = 11.9 Hz), 3.65-3.57 (m, 3H), 3.46 (t , 1H, J = 9.2 Hz), 3.43 (dd, 1H, J = 3.4, J = 9.7 Hz), 3.31 (s, 3H);13C NMR (CDCl3) δ138.6 (C), 137.9 (C), 128.3 (CH), 128.2 (CH), 127.9 (CH), 127.8 (C
H), 127.7 (CH), 127.6 (CH), 127.4 (CH), 98.1 (CH), 81.9 (CH), 80.0 (CH), 75.6 (CH2), 75.0 (CH2), 73.4 (CH2), 70.6 (CH), 61.9 (CH2), 55.2 (CH3).
J = 8.5 Hz), 5.24 (d, 1H, J = 8.0 Hz), 4.75 (d, 1H, J = 12.6 Hz), 4.70 (d, 1H, J = 12.1 Hz), 4.47-4.37 (m, 6H), 4.27 (dd, 1H, J = 8.5 Hz, 10.7 Hz), 4.16 (dd, 1H, J = 8.2 Hz, 10.7 Hz), 4.13-4.03 (m, 3H), 3.75 (t, 1H, J = 10.2 Hz), 3.66 (dd, 1H, J = 4.3 Hz, 10.0 Hz), 3.57 (s, 3H), 3.48 (m, 2H), 3.34 (m, 2H), 3.02 (bs, 1H).
ピングした糖 2 (19.5 mg, 0.031 mmol)を塩化メチレン (1.5 mL) に溶解し、トリフェニルホスフィン (12.2 mg, 0.046 mmol) を加えた。アルゴン雰囲気下4時間撹拌した後、反応液を減圧濃縮した。残渣を塩化メチレン (1.5 mL)、酢酸 (0.3 mL)、水 (0.3 mL) に溶解し、DDQ (10.9 mg, 0.0463 mmol) を0 °Cにて加えた。5分後、アスコルビン酸緩衝液を加え、水層をクロロホルムで抽出した。あわせた有機層を水、飽和食塩水で洗浄し、Na2SO4 を用いて乾燥した。溶媒を減圧濃縮し、残渣をプレパラティブTLC (ヘキサン:酢酸エチル1:1)により精製し、脱保護体 3 (13.6 mg, 70%)を得た。キャッピング体 2 は回収された。(18.5 mg, 95%).
J = 8.5 Hz), 5.15 (t, 1H, J = 9.0 Hz).
Data of 12: 1HNMR δ 5.63 (d, 1H, J = 8.2 Hz), 1.27 (m, 4H).
13のデータ; 1H-NMR δ 5.43 (d, 1H, J = 8.3 Hz), 5.28 (d, 1H, J = 8.0 Hz).
, 5.63 (d, J = 7.8 Hz), 5.43 (d, J = 8.5 Hz), 5.28 (d, J = 8.0 Hz), 5.10 (t , J = 9.7 Hz)
Claims (1)
- エチルイソシアナトホルメート又はエチルイソチオシアナトホルメートと糖又はアルコールとを反応させることによって糖の水酸基をキャッピングする工程を含む、糖鎖の合成方法。
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JP2004363017A JP4726477B2 (ja) | 2004-12-15 | 2004-12-15 | 糖鎖合成におけるキャッピング試薬 |
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JP2004363017A JP4726477B2 (ja) | 2004-12-15 | 2004-12-15 | 糖鎖合成におけるキャッピング試薬 |
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JP2006169157A JP2006169157A (ja) | 2006-06-29 |
JP4726477B2 true JP4726477B2 (ja) | 2011-07-20 |
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EP2145895B1 (en) * | 2008-07-08 | 2013-10-30 | Commissariat à l'Énergie Atomique et aux Énergies Alternatives | Process for the manufacturing of glycochips |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH0873484A (ja) * | 1994-08-31 | 1996-03-19 | Adir | 新規なテトラヒドロピラン化合物、その製造方法、及びそれらを含む薬剤組成物 |
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JPH0873484A (ja) * | 1994-08-31 | 1996-03-19 | Adir | 新規なテトラヒドロピラン化合物、その製造方法、及びそれらを含む薬剤組成物 |
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