D-阿拉伯糖 | 28697-53-2

• 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: D-阿拉伯糖
• 中文别名: D-(-)-树胶醛糖；D-阿拉伯吡喃糖
• 英文名称: D-Arabinose
• 英文别名: D-arabinopyranose；arabinose；(3S,4R,5R)-oxane-2,3,4,5-tetrol
• CAS: 28697-53-2
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: SRBFZHDQGSBBOR-ZRMNMSDTSA-N

物化性质

• 熔点：
  162-164 °C(lit.)
• 比旋光度：
  -103.5 º (c=4, H2O, 24hrs.)
• 沸点：
  191.65°C (rough estimate)
• 密度：
  1.1897 (rough estimate)
• 溶解度：
  H2O:1 Mat 20 °C,透明，无色
• 碰撞截面：
  134.5 Ų [M+Na]+
• 稳定性/保质期：

  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2940000000
• 危险类别码：
  R20/21/22,R36/37/38
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封，在温室中保存

SDS

Name:	D-(-)-Arabinose P.A. Material Safety Data Sheet
Synonym:	None known
CAS:	28697-53-2

Section 1 - Chemical Product MSDS Name:D-(-)-Arabinose P.A. Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
28697-53-2	D-(-)-Arabinose	100.0	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May cause erythema (redness) and edema (fluid buildup) with crusting and scaling.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Non-combustible, substance itself does not burn but may decompose upon heating to produce irritating, corrosive and/or toxic fumes.
Extinguishing Media:
Substance is noncombustible; use agent most appropriate to extinguish surrounding fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 28697-53-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white crystalline powder
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 162-164C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C5H10O5
Molecular Weight: 150.067

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 28697-53-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
D-(-)-Arabinose - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 28697-53-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 28697-53-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 28697-53-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

D-阿拉伯糖是一种单糖，对秀丽隐杆线虫有较强的生长抑制作用，其 IC50 值为 7.5 mM。

化学性质

D-阿拉伯糖为白色结晶，无味。熔点为 162-164℃，相对密度为 1.585，折光率为 1.585，[α]D20 值为 -104.3°（C=3，H2O）。该物质微溶于乙醇，而不溶于甲醇、乙醚或丙酮。

用途

D-阿拉伯糖可作为阿糖胞苷的中间体，并且也可用作生化试剂，用于细菌培养。此外，它还可用作甜味剂。

生产方法

D-阿拉伯糖可以通过葡萄糖酸钙在三价铁离子参与下与过氧化氢反应进行还原制备。同时，也可以从植物中提取得到。

反应信息

• 作为反应物：
  描述：

  D-阿拉伯糖 在 吡啶 、 盐酸 作用下， 反应 5.5h， 生成 methyl tri-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  碘化阿霉素核苷类组织缺氧新标志物的合成和放射性标记。

  摘要：

  已经合成了七种二代碘化阿霉素核苷类缺氧标记物，并在体外和体内测试了肿瘤细胞的缺氧标记活性。β-D-碘阿唑霉素半乳糖苷 (IAZG) 和 β-D-碘阿霉素木吡喃糖苷 (IAZXP) 表现出优于 IAZA 的缺氧标记特性，因为它们具有更高的水溶性、从荷瘤小鼠体内快速清除血浆的速度和最大肿瘤/血液 ( /B) 和肿瘤/肌肉 (T/M) 比率。我们对动物肿瘤模型的研究表明，通过闪烁扫描或平面成像确定的这些标志物的 T/B 或 T/M 比率可以预测肿瘤缺氧的相对程度和肿瘤的放射抗性。© 1997 约翰威利父子公司。

  DOI：

  10.1002/(sici)1099-1344(199707)39:7<541::aid-jlcr5>3.0.co;2-b
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 氧气 、 lithium hydroxide 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以41%的产率得到D-阿拉伯糖
  参考文献：
  名称：

  Degradation of Unprotected Aldohexonic Acids to Aldopentoses Promoted by Light and Oxygen

  摘要：

  Herein reported is a photoredox-catalyzed oxidative degradation reaction of unprotected aldohexonic acids, which are shortened by one-carbon to the corresponding aldopentoses. Oxygen including aerial oxygen is used as a terminal oxidant. The mild reaction conditions permit even disaccharides to successfully undergo the degradation reaction with the glycosidic bond remaining intact. Quinic acid is also converted to a useful chiral synthetic intermediate.

  DOI：

  10.1246/cl.200517
• 作为试剂：
  描述：

  1,3-二氧代丙烷-1,3-二酮 在 D-阿拉伯糖 、 异丙基-beta-D-硫代半乳糖吡喃糖苷 作用下， 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成 3-羟基丙酸
  参考文献：
  名称：

  在基因改造的大肠杆菌菌株中使用新型丙二酰辅酶A介导的生物合成途径生产3-羟基丙酸酯†

  摘要：

  3-羟基丙酸（3-HP）是一种有前途的平台化学品，具有广泛的应用范围。3-HP的传统化学合成方法已经确立，但是所用原料的资源限制，价格昂贵和毒性不符合新的可持续发展目标。因此，主要由于其环境友好的生产，可再生资源的利用和可持续发展，通过发酵微生物合成3-HP将成为一种有前途和有吸引力的途径。在此，为了直接从丙二酸酯生物合成3-HP，成功开发了如下的新丙二酰-CoA介导的生物合成途径。首先，对涉及丙二酸运输的各种运输工具进行了系统的研究和筛选。其次，要生物合成3-HP，Chloroflexus子囊菌从和丙二酰-CoA合成酶（MATB）沼泽红假单胞菌在大肠杆菌C43（DE3）株，将其从三个不同的MATB酶筛选。最后，为了进一步提高3-HP的产量，表达天然的转氢酶（PntAB）和NAD激酶（YfjB）基因以增加大肠杆菌中NADPH的供应。最终的基因改造菌株SGN78在丙二酸利用方面显示出显着改善，并在烧瓶培养物中产生了1

  DOI：

  10.1039/c9gc02286d

文献信息

• Catalytic asymmetric epoxidation
  申请人：——

  公开号：US06348608B1

  公开（公告）日：2002-02-19

  A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.

  一种化合物及其生产方法被披露，该方法使用手性酮和氧化剂从烯烃生产具有对映体富集的环氧乙烷。
• Purification, Characterization, and Molecular Cloning of a Pyranose Oxidase from the Fruit Body of the Basidiomycete,<i>Tricholoma matsutake</i>
  作者：Yoshimitsu TAKAKURA、Shigeru KUWATA

  DOI：10.1271/bbb.67.2598

  日期：2003.1

  A new H2O2-generating pyranose oxidase was purified as a strong antifungal protein from an arbuscular mycorrhizal fungus, Tricholoma matsutake. The protein showed a molecular mass of 250 kDa in gel filtration, and probably consisted of four identical 62 kDa subunits. The protein contained flavin moiety and it oxidized D-glucose at position C-2. H2O2 and D-glucosone produced by the pyranose oxidase reaction showed antifungal activity, suggesting these compounds were the molecular basis of the antifungal property. The Vmax, Km, and kcat for D-glucose were calculated to be 26.6 U/mg protein, 1.28 mM, and 111/s, respectively. The enzyme was optimally active at pH 7.5 to 8.0 and at 50°C. The preferred substrate was D-glucose, but 1,5-anhydro-D-glucitol, L-sorbose, and D-xylose were also oxidized at a moderate level. The cDNA encodes a protein consisting of 564 amino acids, showing 35.1% identity to Coriolus versicolor pyranose oxidase. The recombinant protein was used for raising the antibody.

  从一种内生菌根真菌松口蘑中纯化得到一种新的H2O2生成吡喃糖氧化酶，该酶具有强烈的抗真菌蛋白活性。该蛋白在凝胶过滤中表现出250 kDa的分子质量，可能由四个相同的62 kDa亚基组成。该蛋白含有黄素部分，并在C-2位置氧化D-葡萄糖。由吡喃糖氧化酶反应产生的 和D-葡糖酮具有抗真菌活性，表明这些化合物是其抗真菌特性的分子基础。D-葡萄糖的Vmax、Km和kcat分别为26.6 U/mg蛋白、1.28 mM和111/s。该酶在pH 7.5至8.0和50°C下活性最佳。其首选底物是D-葡萄糖，但1,5-脱水-D-山梨醇、L-山梨糖和D-木糖也能在中等程度上被氧化。该cDNA编码一个由564个氨基酸组成的蛋白质，与杂色革盖菌的吡喃糖氧化酶有35.1%的同源性。使用重组蛋白制备抗体。
• Determination of the absolute configuration of monosaccharides by a colour change in a chiral cholesteric liquid crystal system
  作者：Tony D. James、Takaaki Harada、Seiji Shinkai

  DOI：10.1039/c39930000857

  日期：——

  Cholesterylboronic acid complexes of monosaccharides alter the colour of a composite chiral cholesteric liquid crystal membrane, the direction of the colour change is indicative of the absolute configuration of the monosaccharide.

  单糖的胆甾醇硼酸复合物改变复合手性胆甾型液晶膜的颜色，颜色变化的方向指示单糖的绝对构型。
• Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source
  作者：Thamrongsak Cheewawisuttichai、Robert D. Hurst、Matthew Brichacek

  DOI：10.1016/j.carres.2021.108282

  日期：2021.4

  The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The

  在缓冲水溶液中使用O-苯基羟胺盐酸盐可以有效地将醛转化为腈。报告的方法专门针对包括碳水化合物在内的水溶性底物进行了优化。包括单糖、二糖和甲硅烷基保护的糖在内的几种还原糖以高产率转化为氰醇。反应条件也适用于从各种类型的疏水醛底物形成腈。此外，通过使用易于去除的弱碱性树脂作为促进剂，可以从氰醇中消除氰化物，类似于 Wohl 降解。
• Enzymatic synthesis of β-xylosyl-oligosaccharides by transxylosylation using two β-xylosidases of glycoside hydrolase family 3 from Aspergillus nidulans FGSC A4
  作者：Adiphol Dilokpimol、Hiroyuki Nakai、Charlotte H. Gotfredsen、Maaike Appeldoorn、Martin J. Baumann、Natsuko Nakai、Henk A. Schols、Maher Abou Hachem、Birte Svensson

  DOI：10.1016/j.carres.2010.12.010

  日期：2011.2

  gave inferior yields on these acceptors. The regioselectivity was acceptor dependent and primarily involved beta-1,4 or 1,6 product linkage formation although minor products with different linkages were also obtained. Five of the 18 transxylosylation products obtained from D-lyxose, D-galactose, turanose and sucrose (two products) as acceptors were novel xylosyl-oligosaccharides, beta-D-Xylp-(1-->4)-D-Lyxp

  来自构巢曲霉FGSCA4，BxlA和BxlB的构巢曲霉糖苷水解酶家族3（GH 3）的两个β-木糖苷酶在巴斯德毕赤酵母中重组产生，并分别以16和118mg / L的产率分泌到培养上清液中。BxlA表现出比BxlB高约六倍的催化效率（k（cat）/ K（m））（对聚硝基苯基β-D-木吡喃糖苷（pNPX）和β-1,4-木糖寡糖（聚合度2-6）） 。对于这两种酶，k（cat）/ K（m）随着β-1,4-木糖寡糖链长的增加而降低。使用pNPX作为供体，以9种单糖，7种二糖和两种糖醇作为受体，通过反式木糖基化反应合成了18种不同的β-木糖基-低聚糖，收率为2-36％（BxlA）和6-66％（BxlB）。BxlA使用了单糖D-甘露糖，D-lyxose，D-talose，D-木糖，D-阿拉伯糖，L-岩藻糖，D-葡萄糖，D-半乳糖和D-果糖为受体，而BxlB使用相同的物质，除了D-糖，D-阿拉伯糖和L-岩藻