L-gulono-1,4-lactone | 1128-23-0

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: L-gulono-1,4-lactone
• 英文别名: L-gulonolactone；D-Mannono-γ-lacton；(3S,4R,5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one
• CAS: 1128-23-0；1128-24-1；1198-69-2；1668-08-2；2426-46-2；2782-07-2；3158-30-3；3327-64-8；6322-07-2；10238-03-6；10366-82-2；18404-70-1；22430-23-5；23666-11-7；26301-79-1；29474-78-0；74464-44-1；78184-43-7；83602-36-2；119008-75-2；127997-10-8
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: SXZYCXMUPBBULW-YPNFMUOWSA-N

物化性质

• 熔点：
  187-190 °C(lit.)
• 比旋光度：
  54.5 º (c=2, water 57.5 ºC)
• 沸点：
  230.35°C (rough estimate)
• 密度：
  1.3253 (rough estimate)
• 溶解度：
  DMSO（少量）、甲醇（少量）、水（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

生物活性 L-Gulono-1,4-lactone（L-古洛诺-1,4-乳酸，还原抗坏血酸）是L-gulono-1,4-lactone氧化还原酶的底物，这种酶可催化L-抗坏血酸生物合成过程中的最后一步。

目标
人体内源性代谢物

反应信息

• 作为反应物：
  描述：

  L-gulono-1,4-lactone 生成 (3aR,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
  参考文献：
  名称：

  由L-古洛内酯合成6-表锡精胺和1,6-二甜基葡萄精胺和由D-古洛内酯合成L-6-表锡精胺和L-1,6-二甜基葡萄精胺

  摘要：

  天然产物6-表皮锡精胺[（1S，6R，7R，8R，8aR）-1,6,7,8-四羟基八氢吲哚嗪]和1,6-diepicastastspermine [（1R，6R L-古洛内酯中的1,7R，8R，8aR）-1,6,7,8-四羟基八氢-吲哚嗪和对映体L-6-表锡精胺[（1R，6S，7S，8S，8aS）-1据报道，来自D-古洛内酯的，6,7,8-四羟基八氢吲哚嗪]和L-1,6-二甲基甜精胺[（1S，6S，7S，8S，8aS）-1,6,7,8-四羟基八氢吲哚嗪]。

  DOI：

  10.1016/0040-4039(88)85305-x

文献信息

• Synthesis of some esters and lactones of aldonic acids
  作者：W.J. Humphlett

  DOI：10.1016/s0008-6215(00)82574-4

  日期：1967.4

  formation of esters of aldonic acids by treatment with an alcohol in the presence of an acid depends on the nature of the reagents and on the solubility of the products. The formation of aldonolactones is often a favored, competing reaction. Fully acetylated or benzoylated aldonic esters are formed without these restrictions. Among the products, liquid esters and certain of their acid chloride and

  摘要在酸存在下用醇处理可形成醛糖酸的酯，取决于试剂的性质和产物的溶解度。醛糖内酯的形成通常是有利的竞争反应。在没有这些限制的情况下，形成了完全乙酰化或苯甲酰化的醛糖酸酯。在产物中，液体酯及其某些酰氯和酰胺中间体是可蒸馏的。基于这项研究的结果，描述了一些合成酯和内酯的有效方法。
• Nucleophilic Addition Reaction of 2-Trimethylsilyloxyfuran to <i>N</i>-Gulosyl-<i>C</i>-alkoxymethylnitrones:  Synthetic Approach to Polyoxin C
  作者：Naka Mita、Osamu Tamura、Hiroyuki Ishibashi、Masanori Sakamoto

  DOI：10.1021/ol0200044

  日期：2002.4.1

  [GRAPHICS]The stereoselectivity of nucleophilic addition of 2-trimethylsilyloxyfuran to N-gulosyl-C-alkoxymethylnitrones was investigated. It was found that the selectivity was highly dependent on the bulkiness of the C-substituent of the nitrone. The major adducts were elaborated into the key intermediate of polyoxin C.
• <i>exo</i>-Imino to <i>endo</i>-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars
  作者：Robert M. Moriarty、Carmen I. Mitan、Norica Branzǎ-Nichita、Kenneth R. Phares、Damon Parrish

  DOI：10.1021/ol061071r

  日期：2006.8.1

  A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.
• Synthesis of 6-epicastanospermine and 1,6-diepicastanospermine from L-gulonolactone and synthesis of L-6-epicastanospermine and L-1,6-diepicastanospermine from D-gulonolactone
  作者：George W.J. Fleet、Nigel G. Ramsden、Russell J. Molyneux、Gary S. Jacob

  DOI：10.1016/0040-4039(88)85305-x

  日期：1988.1

  olizine], isolated from Castanospermum australe, and of 1,6-diepicastanospermine [(1R,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyoctahydro-indolizine] from L-gulonolactone and the synthesis of the enantiomers, L-6-epicastanospermine [(1R,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizine] and L-1,6-diepicastanospermine [(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydro-indolizine] from D-gulonolactone are

  天然产物6-表皮锡精胺[（1S，6R，7R，8R，8aR）-1,6,7,8-四羟基八氢吲哚嗪]和1,6-diepicastastspermine [（1R，6R L-古洛内酯中的1,7R，8R，8aR）-1,6,7,8-四羟基八氢-吲哚嗪和对映体L-6-表锡精胺[（1R，6S，7S，8S，8aS）-1据报道，来自D-古洛内酯的，6,7,8-四羟基八氢吲哚嗪]和L-1,6-二甲基甜精胺[（1S，6S，7S，8S，8aS）-1,6,7,8-四羟基八氢吲哚嗪]。