4-hydroxy-2,2'-bipyridine-6-carboxylic acid | 1375241-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-hydroxy-2,2'-bipyridine-6-carboxylic acid
• 英文别名: 4-oxo-6-pyridin-2-yl-1H-pyridine-2-carboxylic acid
• CAS: 1375241-79-4
• 化学式: C₁₁H₈N₂O₃
• 分子量: 216.196
• InChiKey: WKZUELLTDYGSBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2,2'-bipyridine-6-carboxylic acid 、 苯硫酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Investigation of 2,2′-Bipyridine Biosynthesis Reveals a Common Two-Component System for Aldehydes Production by Carboxylate Reduction

  摘要：

  DOI：

  10.1021/acs.orglett.1c04239
• 作为产物：
  描述：

  N-氧代-4-硝基-2，2’联吡啶 在 氢溴酸 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 4-hydroxy-2,2'-bipyridine-6-carboxylic acid
  参考文献：
  名称：

  Investigation of 2,2′-Bipyridine Biosynthesis Reveals a Common Two-Component System for Aldehydes Production by Carboxylate Reduction

  摘要：

  DOI：

  10.1021/acs.orglett.1c04239

文献信息

• Biochemical and Structural Insights into the Aminotransferase CrmG in Caerulomycin Biosynthesis
  作者：Yiguang Zhu、Jinxin Xu、Xiangui Mei、Zhan Feng、Liping Zhang、Qingbo Zhang、Guangtao Zhang、Weiming Zhu、Jinsong Liu、Changsheng Zhang

  DOI：10.1021/acschembio.5b00984

  日期：2016.4.15

  functional characterization, kinetic analysis, substrate specificity, and structure insights of an aminotransferase CrmG in 1 biosynthesis. The aminotransferase CrmG was confirmed to catalyze a key transamination reaction to convert an aldehyde group to an amino group in the 1 biosynthetic pathway, preferring l-glutamate and l-glutamine as the amino donor substrates. The crystal structures of CrmG in

  Caerulomycin A（CRM A 1）属于含有2,2'-联吡啶基环核心结构的天然产物家族，目前正在开发作为有效的新型免疫抑制剂。在这里，我们报告氨基转移酶CrmG在1生物合成中的功能表征，动力学分析，底物特异性和结构见解。转氨酶CrmG确认以催化关键氨基转移反应成醛基转化成氨基中的1种生物合成途径，宁愿升谷氨酸盐和升-谷氨酰胺作为氨基供体底物。CrmG的晶体结构与5'-磷酸吡ox醛磷酸盐（PLP）或5'-磷酸吡ox胺磷酸盐（PMP）或受体底物复合形成的晶体结构经确定采用PLP依赖型酶的典型折叠I型，且具有独特的小附加域。结构指导的定点诱变确定了底物结合和催化活性的关键氨基酸残基，从而为CrmG的转氨机制提供了见识。
• Acyclic Congeners from <i>Actinoalloteichus cyanogriseus</i> Provide Insights into Cyclic Bipyridine Glycoside Formation
  作者：Peng Fu、Yiguang Zhu、Xiangui Mei、Yi Wang、Haijian Jia、Changsheng Zhang、Weiming Zhu

  DOI：10.1021/ol5019757

  日期：2014.8.15

  Inactivation of the O-methyltransferase gene crmM of Actinoalloteichus cyanogriseus WH1-2216-6 led to a mutant that produced three new acyclic bipyridine glycosides, cyanogrisides E-G (1-3). Further chemical analysis of the wild strain yielded 1 and another new analogue, cyanogriside H (4). Compounds 1-4 possess a skeleton consisting of a 2,2'-bipyridine and a d-quinovose or l-rhamnose sugar moiety. Cyanogriside G (3) was considered to be a key biosynthetic intermediate of the cyclic bipyridine glycosides cyanogrisides A-D. Compounds 2 and 3 showed cytotoxicities against HCT116 and HL-60 cells, and compounds 1 and 4 were cytotoxic on K562 cells.
• Identification of Caerulomycin A Gene Cluster Implicates a Tailoring Amidohydrolase
  作者：Yiguang Zhu、Peng Fu、Qinheng Lin、Guangtao Zhang、Haibo Zhang、Sumei Li、Jianhua Ju、Weiming Zhu、Changsheng Zhang

  DOI：10.1021/ol300589r

  日期：2012.6.1

  The biosynthetic gene cluster for caerulomycin A (1) was cloned and characterized from the marine actinomycete Actinoalloteichus cyanogriseus WH1-2216-6, which revealed an unusual hybrid polyketide synthase (PKS)/nonribosomal peptide synthetase (NRPS) system. The crmL disruption mutant accumulated caerulomycin L (2) with an extended L-leucine at C-7, implicating an amidohydrolase activity for CrmL. The leucine-removing activity was confirmed for crude CrmL enzymes. Heterologous expression of the 1 gene cluster led to 1 production in Streptomyces coelicolor.
• Investigation of 2,2′-Bipyridine Biosynthesis Reveals a Common Two-Component System for Aldehydes Production by Carboxylate Reduction
  作者：Ming Chen、Bo Pang、Wenping Ding、Qunfei Zhao、Zhijun Tang、Wen Liu

  DOI：10.1021/acs.orglett.1c04239

  日期：2022.1.28