L(+)-赤藓酮糖(水合) | 533-50-6

• 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 - 有机氧化合物
• 中文名称: L(+)-赤藓酮糖(水合)
• 中文别名: L-(+)-赤藓酮糖；L-赤藻酮糖；L-赤藓酮糖；(3S)-1,3,4-三羟基-2-丁酮
• 英文名称: L-erythrulose
• 英文别名: erythrulose；L-(S)-erythrulose；(S)-erythrulose；(3S)-1,3,4-trihydroxy-butan-2-one；(3S)-1,3,4-trihydroxybutan-2-one
• CAS: 533-50-6
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: UQPHVQVXLPRNCX-VKHMYHEASA-N

物化性质

• 比旋光度：
  D18 +11.4° (c = 2.4 in water)
• 沸点：
  144.07°C (rough estimate)
• 密度：
  1.420
• 闪点：
  110℃
• 溶解度：
  甲醇（微溶）、水（微溶）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914400090
• 储存条件：
  存储温度应控制在2-8°C，并请避免光照直射。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : L-(+)-Erythrulose
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 533-50-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : L-Glycero-2-tetrulose
S-1,3,4-Trihydroxy-2-butanone
Formula : C4H8O4
Molecular Weight : 120,10 g/mol
CAS-No. : 533-50-6
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Hygroscopic. Store under inert gas.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: clear, viscous liquid
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point 110 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 1,391 g/cm3
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  L(+)-赤藓酮糖(水合) 在 Saccharomyces cerevisiae transketolase 、 3-[(4-氨基-2-甲基-5-嘧啶基)甲基]-4-甲基-5-[4,6,6-三羟基-4,6-二氧-3,5-二氧-4,6-二磷(五)己-1-基]噻唑-3-鎓 、 magnesium 作用下， 以 aq. phosphate buffer 为溶剂， 生成 羟乙醛
  参考文献：
  名称：

  将热力学与动力学分开—对转酮醇酶反应的新理解

  摘要：

  转酮醇酶催化两种高极性化合物的不对称C-C键形成。在过去的30年中，该反应在文献中被一致描述为不可逆的，因为如果使用羟基丙酮酸锂（LiHPA）作为底物会伴随释放CO 2。然而，经过较长时间的反应后，我们现在发现它最初是动力学控制的。与先前的建议相反，对于合成更有趣的非极性底物的非自然转化，因此不需要完全改变活性部位的极性。从对接研究中发现，水和氢键网络对于底物结合必不可少，因此可以使脂肪醛在转酮酶的带电活性位点转化。

  DOI：

  10.1002/cctc.201601649
• 作为产物：
  描述：

  羟乙醛 在 magnesium(II) chloride hexahydrate 、 焦磷酸硫胺素 、 recombinant Geobacillus stearothermophilus transketolase H₁₀₂L/L₁₁₈I/H₄₇₄S mutant 作用下， 以 aq. phosphate buffer 为溶剂， 生成 L(+)-赤藓酮糖(水合)
  参考文献：
  名称：

  转酮酶变体催化醛的交叉偶姻缩合用于合成脂肪族 α-羟基酮

  摘要：

  我们证明来自嗜热脂肪地芽孢杆菌的转酮醇酶变体催化涉及两个羟基化或非脂肪族醛的偶姻缩合反应。这种混杂的 TK 催化反应为通常 TK 机制中用作供体底物的 α-酮酸的酮醇转移提供了一种有吸引力的替代方案，通过避免二氧化碳释放来增加原子经济性。转酮醇酶变体 H102L/L118I/H474G(S) 对丙醛和较小程度的乙醛的自缩合表现出从头活性，并且具有控制与丙醛更具挑战性的交叉偶姻缩合反应的选择性的显着能力或异丁醛用作亲核试剂，不同的羟基化醛（C2-C4）用作亲电试剂。由化学计量的醛合成七种脂肪族对称和不对称 α-羟基酮，其产率与基于 α-酮酸脱羧的常见 TK 反应获得的产率相似。这种新颖的酶促交叉偶姻缩合反应扩展了合成不对称脂肪族 α-羟基酮的工具箱，同时改进了先前酶促和化学策略的质量指标。

  DOI：

  10.1039/d4gc01373e
• 作为试剂：
  描述：

  2-氨基噻唑 、 1,3-二羟基丙酮 在 L(+)-赤藓酮糖(水合) 作用下， 以 水 为溶剂， 反应 552.0h， 以56%的产率得到3,3-Bis(thiazol-2-ylamino)propane-1,2-diol
  参考文献：
  名称：

  益生元从复杂混合物中选择和组装蛋白原氨基酸和天然核苷酸

  摘要：

  益生元合成生物氨基酸和核苷酸的主要问题是避免伴随合成不希望的或不相关的副产物。另外，多步路径需要能够使反应物顺序添加和纯化中间体的机制，这与合理的地球化学情况一致。在这里，我们表明2-氨基噻唑与二碳糖和三碳糖（分别为甘醇醛和甘油醛）选择性反应，从而导致它们的积累和纯化为稳定的结晶类缩醛胺。这允许甚至从复杂的糖混合物中合成核糖核苷酸。值得注意的是 氨醛的形成还克服了甘油醛热力学上有利于异构化为二羟基丙酮的异构化问题，因为只有甘油醛的氨醛才从平衡混合物中分离出来。最后，我们表明氨基形成为氨基酸提供了一种新颖的途径，从而避免了非蛋白质生成的α，α-二取代类似物的合成。控制益生元混合物中蛋白质氨基酸和核糖核苷酸装配的常见物理化学机制表明，这些必需的代谢物类别具有统一的化学起源。

  DOI：

  10.1038/nchem.2703

文献信息

• A Mutant D-Fructose-6-Phosphate Aldolase (Ala129Ser) with Improved Affinity towards Dihydroxyacetone for the Synthesis of Polyhydroxylated Compounds
  作者：José A. Castillo、Christine Guérard-Hélaine、Mariana Gutiérrez、Xavier Garrabou、Martine Sancelme、Melanie Schürmann、Tomoyuki Inoue、Virgil Hélaine、Franck Charmantray、Thierry Gefflaut、Laurence Hecquet、Jesús Joglar、Pere Clapés、Georg A. Sprenger、Marielle Lemaire

  DOI：10.1002/adsc.200900772

  日期：——

  is particularly useful in carboligation multi‐step cascade synthesis of polyhydroxylated complex compounds. Production of the mutant protein was also improved for its convenient use in synthesis. Several carbohydrates and nitrocyclitols were efficiently prepared, demonstrating the versatile potential of FSA A129S as biocatalyst in organic synthesis.

  研究了大肠杆菌D-果糖-6-磷酸醛缩酶（FSA）的突变体FSA A129S，其对醛醇加成反应中供体底物二羟基丙酮（DHA）的催化效率得到了提高，可用于合成应用。FSA A129S的DHA的k cat / K M值比FSA野生型（FSA wt）高出17倍。另一方面，对于羟丙酮作为供体底物，发现FSA A129S的效率比FSA wt低3.5倍。此外，FSA A129S还接受了乙醇醛（GA）作为供体底物，其亲和力比FSA wt低3.3倍。两种FSA wt的差异选择性FSA A129S和GA的FSA A129S使它们成为互补的生物催化剂，可以控制供体和受体的作用，这在多羟基化复合化合物的碳多步级联碳多步合成中特别有用。突变蛋白的生产也得到了改进，因为它可方便地用于合成。有效地制备了几种碳水化合物和硝基环糖醇，证明了FSA A129S作为有机合成中的生物催化剂具有多种用途。
• Thermostable Transketolase from<i>Geobacillus stearothermophilus:</i>Characterization and Catalytic Properties
  作者：Juliane Abdoul-Zabar、Isabelle Sorel、Virgil Hélaine、Franck Charmantray、Titu Devamani、Dong Yi、Véronique de Berardinis、Dominique Louis、Philippe Marlière、Wolf-Dieter Fessner、Laurence Hecquet

  DOI：10.1002/adsc.201200590

  日期：2013.1.14

  Here we have characterized the first transketolase (TK) from a thermophilic microorganism, Geobacillus stearothermophilus, which was expressed from a synthetic gene in Escherichia coli. The G. stearothermophilus TK (mTKgst) retained 100% activity for one week at 50 °C and for 3 days at 65 °C, and has an optimum temperature range around 60–70 °C, which will be useful for preparative applications and

  在这里，我们表征了嗜热微生物嗜热脂肪地芽孢杆菌的第一个转酮酶（TK），该酶是由大肠杆菌中的合成基因表达的。在G.嗜热脂肪TK（MTK GST）保持100％活性一周，在50℃，并在65℃下3天，并且具有最佳温度范围约60-70℃，这将是制备应用和有用用于未来的生物催化剂开发。mTK gst的热稳定性使我们能够通过在65°C的温度下对粗细胞提取物进行热激处理45分钟，轻松地进行一步纯化，从而从1 L培养物中直接产生132 mg的纯mTK gst。mTK的反应速率GST与乙醇醛高出14倍，在70℃比在20℃下，和高4倍，在50℃时相比，大肠杆菌相同的条件下TK。当在50°C下用其他醛作为受体进行测试时，mTK gst活性比在20°C下获得的mTK gst活性高约3倍。这项新的传统知识在生物催化中的应用是以羟基丙酮酸为供体，三种醛为受体，分别是乙醇醛，D-甘油醛和丁醛，其中相应的产物L-赤藓糖1，D-木酮糖2和1
• On the Way to Glycoprocessing Inhibitors: A General One-Pot Synthesis of Imidazolosugars
  作者：Jacques Streith、Arnaud Boiron、Andrzej Frankowski、Didier Le Nouen、Hélène Rudyk、Théophile Tschamber

  DOI：10.1055/s-1995-4040

  日期：1995.8

  Reaction of several monosaccharides with formamidine acetate afforded the corresponding imidazolosugars 5-11 in 30-50% yield.

  几种单糖与甲酰胺乙酸反应，在30-50%的产率下得到了相应的咪唑糖5-11。
• A metagenomics approach for new biocatalyst discovery: application to transaminases and the synthesis of allylic amines
  作者：Damien Baud、Jack W. E. Jeffries、Thomas S. Moody、John M. Ward、Helen C. Hailes

  DOI：10.1039/c6gc02769e

  日期：——

  Transaminase enzymes have significant potential for the sustainable synthesis of amines using mild aqueous reaction conditions. Here a metagenomics mining strategy has been used for new transaminase enzyme discovery. Starting...

  转氨酶具有使用温和的水性反应条件可持续合成胺的巨大潜力。在这里，宏基因组学的挖掘策略已用于新的转氨酶的发现。开始...
• Chiral Polyol Synthesis Catalyzed by a Thermostable Transketolase Immobilized on Layered Double Hydroxides in Ionic liquids
  作者：Ghina Ali、Thomas Moreau、Claude Forano、Christine Mousty、Vanessa Prevot、Franck Charmantray、Laurence Hecquet

  DOI：10.1002/cctc.201500524

  日期：2015.10

  was tested in 30 % [BMIm][Cl] for the synthesis of a rare, very costly commercially available sugar, d‐sedoheptulose, which was obtained in one step from d‐ribose with an isolated yield of 82 %. This biohybrid was reusable over four cycles with no loss of enzymatic activity. The particular activity of free and immobilized TKgst in [BMIm][Cl] holds promise to extend the applications of TKgst in other ionic

  在这项工作中，我们着手研究在离子液体中作为助溶剂的嗜热脂肪热地芽孢杆菌（TK gst）的热稳定转酮醇酶（TK）的活性，该酶以前从未进行过研究。在水中30–50％范围内的1-丁基-3-甲基咪唑鎓氯化物（[BMIm] [Cl]）保持TK gst的总活性，并在存在戊糖作为受体底物（尤其是d-核糖）的情况下提高了反应速率。为了改善合成工艺，TK gst被固定在无机载体层状双氢氧化物（LDHs）上，采用简单，生态兼容，有效的共沉淀程序，具有优异的固定产率和催化活性。生物杂合MgAl @ TKgst在30％[BMIm] [Cl]中进行了测试，用于合成稀有的，非常昂贵的市售糖d-七羟庚糖，该糖是从d-核糖一步获得的，分离产率为82％。该生物杂交体可在四个周期内重复使用，而不会丧失酶活性。[BMIm] [Cl]中游离的固定化TK gst的特殊活性有望扩展TK gst在其他离子液体和生物催化中非常规介质中的应用。