rac-4-benzoylamino-3-hydroxybutyric acid | 91134-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: rac-4-benzoylamino-3-hydroxybutyric acid
• 英文别名: acide benzamido-4 hydroxy-3 butanoique；4-benzoylamino-3-hydroxy-butyric acid；4-Benzoylamino-3-hydroxy-buttersaeure；N-benzoyl-4-amino-3-hydroxybutyric acid；4-Benzamido-3-hydroxybutanoic acid
• CAS: 91134-04-2
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: SHNANTBQDCWKCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-4-benzoylamino-3-hydroxybutyric acid 在 氯化亚砜 作用下， 生成 (2-phenyl-4,5-dihydro-oxazol-5-yl)-acetic acid
  参考文献：
  名称：

  Bergmann; Brand; Weinmann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1923, vol. 131, p. 12

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3-cyano-2-hydroxy-propyl)-benzamide 在 盐酸 作用下， 生成 rac-4-benzoylamino-3-hydroxybutyric acid
  参考文献：
  名称：

  Bergmann; Brand; Weinmann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1923, vol. 131, p. 12

  摘要：

  DOI：

文献信息

• The UDPase activity of the Kluyveromyces lactis Golgi GDPase has a role in uridine nucleotide sugar transport into Golgi vesicles
  作者：M. D. Lopez-Avalos、D. Uccelletti、C. Abeijon、C. B. Hirschberg

  DOI：10.1093/glycob/11.5.413

  日期：2001.5.1

  In Saccharomyces cerevisiae a Golgi lumenal GDPase (ScGda1p) generates GMP, the antiporter required for entry of GDP-mannose, from the cytosol, into the Golgi lumen. Scgda1 deletion strains have severe defects in N- and O-mannosylation of proteins and glycosphingolipids. ScGda1p has also significant UDPase activity even though S. cerevisiae does not utilize uridine nucleotide sugars in its Golgi lumen. Kluyveromyces lactis, a species closely related to S. cerevisiae, transports UDP-N-acetylglucosamine into its Golgi lumen, where it is the sugar donor for terminal N-acetylglucosamine of the mannan chains. We have identified and cloned a K. lactis orthologue of ScGda1p. KlGda1p is 65% identical to ScGda1p and shares four apyrase conserved regions with other nucleoside diphosphatases. KlGda1p has UDPase activity as ScGda1p. Transport of both GDP-mannose, and UDP-GlcNAc was decreased into Golgi vesicles from Klgda1 null mutants, demonstrating that KlGda1p generates both GMP and UMP required as antiporters for guanosine and uridine nucleotide sugar transport into the Golgi lumen. Membranes from Klgda1 null mutants showed inhibition of glycosyltransferases utilizing uridine- and guanosine-nucleotide sugars, presumably due to accumulation of nucleoside diphosphates because the inhibition could be relieved by addition of apyrase to the incubations. KlGDA1 and ScGDA1 restore the wild-type phenotype of the other yeast gda1 deletion mutant. Surprisingly, KlGDA1 has only a role in O-glycosylation in K. lactis but also complements N-glycosylation defects in S. cerevisiae. Deletion mutants of both genes have altered cell wall stability and composition, demonstrating a broader role for the above enzymes.

  在酿酒酵母（Saccharomyces cerevisiae）中，高尔基体腔内 GDP 酶（ScGda1p）生成 GMP，这是 GDP-甘露糖从细胞质进入高尔基体腔所需的反转运体。Scgda1 基因缺失株在蛋白质和糖磷脂的 N- 和 O-mannosyl 化方面存在严重缺陷。尽管 S. cerevisiae 在高尔基体腔内不利用尿苷核苷酸糖，但 ScGda1p 也具有显著的尿苷核苷酸酶活性。乳酸克鲁维酵母菌（Kluyveromyces lactis）是一种与麦角菌（S. cerevisiae）亲缘关系很近的菌种，它将 UDP-N-乙酰葡糖胺转运到高尔基管腔中，作为甘露聚糖链末端 N-乙酰葡糖胺的供糖体。我们发现并克隆了 K. lactis 的 ScGda1p 同源物。KlGda1p与ScGda1p有65%的相同之处，并与其他核苷二磷酸酶共享四个apyrase保守区。KlGda1p 与 ScGda1p 一样具有 UDP 酶活性。在 Klgda1 空缺突变体的高尔基体囊泡中，GDP-甘露糖和 UDP-GlcNAc 的转运都有所减少，这表明 KlGda1p 产生的 GMP 和 UMP 都是鸟苷酸和尿苷核苷酸糖转运到高尔基体内腔所需的反转运体。来自 Klgda1 空缺突变体的膜显示出对利用尿苷和鸟苷酸核苷酸糖的糖基转移酶的抑制，这可能是由于核苷二磷酸盐的积累，因为在培养液中加入 apyrase 可以缓解抑制作用。KlGDA1 和 ScGDA1 恢复了另一种酵母 gda1 缺失突变体的野生型表型。令人惊讶的是，KlGDA1在乳酸酵母中只起O-糖基化作用，但在酿酒酵母中却能补充N-糖基化缺陷。这两个基因的缺失突变体都改变了细胞壁的稳定性和组成，表明上述酶具有更广泛的作用。
• Composition containing a penem or carbapenem antibiotic
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0226304B1

  公开（公告）日：1991-08-28
• Tomita; Sendju, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1927, vol. 169, p. 266
  作者：Tomita、Sendju

  DOI：——

  日期：——
• Srairi, Driss; Maurey, Georges, Bulletin de la Societe Chimique de France, 1987, # 2, p. 297 - 301
  作者：Srairi, Driss、Maurey, Georges

  DOI：——

  日期：——
• Bergmann; Brand; Weinmann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1923, vol. 131, p. 12
  作者：Bergmann、Brand、Weinmann

  DOI：——

  日期：——