2-keto-4-hydroxybutyric acid | 22136-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-keto-4-hydroxybutyric acid
• 英文别名: 2-Keto-4-hydroxybuttersaeure；4-Hydroxy-2-oxobutanoic acid
• CAS: 22136-38-5
• 化学式: C₄H₆O₄
• mdl: MFCD19228631
• 分子量: 118.089
• InChiKey: PUWWONYMIXRVQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-keto-4-hydroxybutyric acid 在 glucose dehydrogenase 、 乙二胺四乙酸 、 2,3,4,5,6-pentahydroxy-hexanal 、 β-nicotinamide-adenine dinucleotide phosphate 、 E_. coli ketopantoate reductase 作用下， 以99.9%的产率得到
  参考文献：
  名称：

  串联羟醛加成和羰基还原生物催化合成同手性 2-羟基-4-丁内酯衍生物

  摘要：

  手性 2-羟基酸和 2-羟基-4-丁内酯衍生物是精细化学品和商品化学品中常见的结构基序。在这里，我们报告了使用三种立体选择性醛缩酶和两种立体互补酮还原酶使用简单和非手性起始材料制备这些化合物的串联生物催化立体发散途径。该策略包括 (i) 使用来自大肠杆菌的两种醛缩酶、3-甲基-2-氧代丁酸羟甲基转移酶 (KPHMT Ecoli )、2-keto-3-deoxy- l- rhamnonate 醛缩酶 (YfaU) 将 2-含氧酸与醛进行醛醇加成反应大肠杆菌）和来自恶臭假单胞菌的反式-o-羟基亚苄基丙酮酸水合酶-醛缩酶(HBPA Pputida ) 和 (ii) 随后通过来自大肠杆菌(KPR Ecoli )的酮泛解酸还原酶和来自假单胞菌的 Δ 1 -piperidine-2-carboxylate/Δ 1 -pyrroline-2-carboxylate 还原酶对羟醛加合物的 2-氧代还原丁香树_

  DOI：

  10.1021/acscatal.3c00367
• 作为产物：
  描述：

  DL-高丝氨酸 在 sodium acetate buffer 、 吡哆醛盐酸盐 、 copper dichloride 作用下， 反应 0.33h， 生成 2-keto-4-hydroxybutyric acid
  参考文献：
  名称：

  Analysis of Glycated and Ascorbylated Proteins by Gas Chromatography−Mass Spectrometry

  摘要：

  Proteins or poly-L-lysine which were incubated in the presence of ascorbic acid dehydroascorbic acid (ascorbylation), or various sugars (glycation) were analyzed by gas chromatography-mass spectrometry (GC-MS) To also detect more labile reaction products, the Maillard modified proteins or poly-L-lysine were enzymatically hydrolyzed and reacted with N-methyl N-(tert-butyldimethylsilyl) trifluoroacetamide to form the N(O)-tert-butyldimethylsilyl (tBDMS) derivatives prior to GC analysis Under these conditions, the known Maillard products N-epsilon-(carboxymethyl)lysine (1), oxalic acid mono N-epsilon lysinylamide (2) and N-epsilon-(carboxyethyl)lysine (3) could be simultaneously detected and quantified in glycated and ascorbylated proteins Additionally, N-epsilon (1-carboxy 3 hydroxypropyl)-L-lysine (4) was identified for the first time as a Maillard product of proteins Under the conditions applied here, 4 was found only in ascorbylated proteins or Poly L lysine, but not in glycated proteins Maillard modified poly-L-lysine was further subjected to high-performance liquid chromatography (HPLC) analysis after enzymatic hydrolysis and formation of the phenyl isothiocyanate derivatized amino acids Using this method, N-epsilon-formyl-L-lysine (5), which cannot be distinguished from 2 by GC-MS analysis, was identified for the first time as a glycation product Compound 5 is mainly formed from ribose, lactose and fructose The indicated Maillard products were quantified in beta lactoglobulin (GC-MS) or poly-L lysine (HPLC) which were glycated or ascorbylated using different precursors.

  DOI：

  10.1021/jf020411u

文献信息

• Analysis of Glycated and Ascorbylated Proteins by Gas Chromatography−Mass Spectrometry
  作者：Katrin Hasenkopf、Birgit Rönner、Hartmut Hiller、Monika Pischetsrieder

  DOI：10.1021/jf020411u

  日期：2002.9.1

  Proteins or poly-L-lysine which were incubated in the presence of ascorbic acid dehydroascorbic acid (ascorbylation), or various sugars (glycation) were analyzed by gas chromatography-mass spectrometry (GC-MS) To also detect more labile reaction products, the Maillard modified proteins or poly-L-lysine were enzymatically hydrolyzed and reacted with N-methyl N-(tert-butyldimethylsilyl) trifluoroacetamide to form the N(O)-tert-butyldimethylsilyl (tBDMS) derivatives prior to GC analysis Under these conditions, the known Maillard products N-epsilon-(carboxymethyl)lysine (1), oxalic acid mono N-epsilon lysinylamide (2) and N-epsilon-(carboxyethyl)lysine (3) could be simultaneously detected and quantified in glycated and ascorbylated proteins Additionally, N-epsilon (1-carboxy 3 hydroxypropyl)-L-lysine (4) was identified for the first time as a Maillard product of proteins Under the conditions applied here, 4 was found only in ascorbylated proteins or Poly L lysine, but not in glycated proteins Maillard modified poly-L-lysine was further subjected to high-performance liquid chromatography (HPLC) analysis after enzymatic hydrolysis and formation of the phenyl isothiocyanate derivatized amino acids Using this method, N-epsilon-formyl-L-lysine (5), which cannot be distinguished from 2 by GC-MS analysis, was identified for the first time as a glycation product Compound 5 is mainly formed from ribose, lactose and fructose The indicated Maillard products were quantified in beta lactoglobulin (GC-MS) or poly-L lysine (HPLC) which were glycated or ascorbylated using different precursors.
• Biocatalytic Synthesis of Homochiral 2-Hydroxy-4-butyrolactone Derivatives by Tandem Aldol Addition and Carbonyl Reduction
  作者：Carlos J. Moreno、Karel Hernández、Samantha Gittings、Michael Bolte、Jesús Joglar、Jordi Bujons、Teodor Parella、Pere Clapés

  DOI：10.1021/acscatal.3c00367

  日期：2023.4.21

  hydroxymethyltransferase (KPHMTEcoli), 2-keto-3-deoxy-l-rhamnonate aldolase (YfaUEcoli), and trans-o-hydroxybenzylidene pyruvate hydratase-aldolase from Pseudomonas putida (HBPAPputida) and (ii) subsequent 2-oxogroup reduction of the aldol adduct by ketopantoate reductase from E. coli (KPREcoli) and a Δ1-piperidine-2-carboxylate/Δ1-pyrroline-2-carboxylate reductase from Pseudomonas syringae pv. tomato DSM 50315

  手性 2-羟基酸和 2-羟基-4-丁内酯衍生物是精细化学品和商品化学品中常见的结构基序。在这里，我们报告了使用三种立体选择性醛缩酶和两种立体互补酮还原酶使用简单和非手性起始材料制备这些化合物的串联生物催化立体发散途径。该策略包括 (i) 使用来自大肠杆菌的两种醛缩酶、3-甲基-2-氧代丁酸羟甲基转移酶 (KPHMT Ecoli )、2-keto-3-deoxy- l- rhamnonate 醛缩酶 (YfaU) 将 2-含氧酸与醛进行醛醇加成反应大肠杆菌）和来自恶臭假单胞菌的反式-o-羟基亚苄基丙酮酸水合酶-醛缩酶(HBPA Pputida ) 和 (ii) 随后通过来自大肠杆菌(KPR Ecoli )的酮泛解酸还原酶和来自假单胞菌的 Δ 1 -piperidine-2-carboxylate/Δ 1 -pyrroline-2-carboxylate 还原酶对羟醛加合物的 2-氧代还原丁香树_