SYNTHESES OF THE ANALOGUES AND THE KETOSIDE DERIVATIVES OF SIALIC ACID,KDO,AND KDN.

唾液酸、KDO 和 KDN 的类似物和酮苷衍生物的合成。

• 批准号: 06651014
• 负责人: SATO Ken-ichi
• 金额: $ 0.77万
• 依托单位: KANAGAWA UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1994
• 资助国家: 日本
• 起止时间: 1994 至 1995
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-06651014/
• 关键词: KDO; KDN; SIALIC ACID; ANALOGUE; GLYCOSYLATION

1. The biologically important terminal units of lipopolysaccharides, 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN), and 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid (N-acetylneuraminic acid, NANA) were synthesized by the use of amino type Horner-Witting reaction. On the basis of above knowledge, ulosonic acid analogues such as 3-deoxy-D-arabino-2-heptulosonic acid and 3-deoxy-D-gluco-2-octulosonic acid were also synthesized. Merit of this method is to select the amino protecting group [such as benzyloxycarbonyl (Cbz) and t-butoxycarbonyl (Boc) ] of witting reagent. As a result, we can select the protecting group, which is needed, for the protection of hydroxyl group of starting materials. This newly developed methods by the use of stable Horner-Witting reagent will provide a route to large scale synthesis of ulosonic acid derivatives.2. By the use of the above knowleges, 5-epi-KDN derivative was also synthesized for synthesizing C-5 modified analogs of KDN and ^<15>N -labeled sialic acid (NANA).

1.利用氨基型霍纳-威廷反应合成了具有重要生物学意义的内毒素末端基团3-脱氧-D-甘露-2-辛酸、3-脱氧-D-甘油-D-半乳糖-2-非磺酸和5-acetamido-3，5-dideoxy-D-glycero-D-galacto-2-nonulosonic酸(N-乙酰神经氨酸，NANA)。在此基础上，合成了3-脱氧-D-阿拉伯基-2-庚磺酸和3-脱氧-D-葡萄糖-2-辛酸等磺酸类似物。该方法的优点是选择试剂的氨基保护基团[如苄氧基羰基(CBZ)和叔丁氧基羰基(Boc)]。因此，我们可以选择所需的保护基团来保护原料的羟基。这一新开发的方法使用稳定的Horner-Witing试剂，将为大规模合成磺酸衍生物提供一条途径。利用上述知识，还合成了5-epi-kdN衍生物，用于合成C-5修饰的kdN类似物和N标记唾液酸(NaNA)。

项目成果

K. Sato: "Convenient Syntheses of 3-Deoxy-D-mannno-2-octulosonic Acid(KDO) and 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Derivatives from D-Mannose." Chem. Lett.129-132 (1994)

K. Sato：“从 D-甘露糖中便捷合成 3-脱氧-D-甘露糖-2-辛糖酸 (KDO) 和 3-脱氧-D-甘油-D-半乳糖-2-非糖糖酸 (KDN) 衍生物。”

K.SATO: "CONVENIENT SYNTHESES OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN) DERIVATIVES FROM D-MANNOSE" CHEM.LETT.129-132 (1994)

K.SATO：“从 D-甘露糖中方便合成 3-脱氧-D-甘露糖酸 (KDO) 和 3-脱氧-D-甘油-D-半乳糖-2-非努糖酸 (KDN) 衍生物”化学

佐藤憲一: "糖鎖合成における重要ユニットの簡便な合成法の開発" 化学工業. 45. 58-66 (1994)

Kenichi Sato：“糖链合成中重要单元的简单合成方法的开发” Kagaku Kogyo。 45. 58-66 (1994)

K.Sato: "Convenient Syntheses of 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Derivatives from D-Mannose." Chem.Lett.129-132 (1994)

K.Sato：“从 D-甘露糖中便捷合成 3-脱氧-D-甘露糖-2-辛糖酸 (KDO) 和 3-脱氧-D-甘油-D-半乳糖-2-非糖糖酸 (KDN) 衍生物。”

K.SATO: "CONVENIENT METHODS FOR SYNTHESIZING VALUABLE SUGAR UNITS IN SYNTHESIZING SUGAR CHAINS" KAGAKU KOGYO. 45. 58-66 (1994)

K.SATO：“在合成糖链中合成有价值的糖单元的便捷方法”KAGAKU KOGYO。