2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 | 10036-64-3

• 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: 2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖
• 中文别名: 2-乙酰氨基-2-脱氧-ALPHA-D-吡喃葡萄糖；2-乙酰氨基-2-脱氧-alpha-d-吡喃葡萄糖；乙酰氨基-联氧-古氨酶；2-乙酰氨基-2-脱氧-α-D-吡喃糖
• 英文名称: N-acetyl-D-glucosamine
• 英文别名: N-acetylglucosamine；2-acetamido-2-deoxy-α-D-glucopyranose；GlcNAc；2-Acetamido-2-deoxy-alpha-D-glucopyranose；N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 10036-64-3
• 化学式: C₈H₁₅NO₆
• 分子量: 221.21
• InChiKey: OVRNDRQMDRJTHS-PVFLNQBWSA-N

物化性质

• 熔点：
  211 °C
• 沸点：
  595.4±50.0 °C(Predicted)
• 密度：
  1.50
• LogP：
  -2.314 (est)
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  29329900
• 储存条件：
  存放在4°C阴凉干燥处

SDS

Name:	2-Acetamido-2-Deoxy-alpha-D-Glucopyranose 99.5+% Material Safety Data Sheet
Synonym:	N-Acetyl-alpha-D-glucosamine
CAS:	10036-64-3

Section 1 - Chemical Product MSDS Name:2-Acetamido-2-Deoxy-alpha-D-Glucopyranose 99.5+% Material Safety Data Sheet
Synonym:N-Acetyl-alpha-D-glucosamine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10036-64-3	2-Acetamido-2-Deoxy-alpha-D-Glucopyran	99.5	233-115-1

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.
Ingestion:
Ingestion of large amounts may cause gastrointestinal irritation.
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: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
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.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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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 general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 10036-64-3: 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 and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 211 deg C
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 211 deg C
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C8H15NO6
Molecular Weight: 221.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, strong acids, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10036-64-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Acetamido-2-Deoxy-alpha-D-Glucopyranose - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 10036-64-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10036-64-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10036-64-3 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

该化合物2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖主要用于科研。

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 在 sodium hydride 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 、 原甲酸三乙酯 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 34.0h， 生成 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[(R)-1-(methoxycarbonyl)ethyl]-α-D-glucopyranoside
  参考文献：
  名称：

  An improved total synthesis of UDP-N-acetyl-muramic acid

  摘要：

  Biochemical testing for novel inhibitors of Mur ligases requires several commercially unavailable and structurally complex substrates. We describe a modified synthetic strategy for the total chemical synthesis of the MurC ligase substrate UDP-Nacetyl-muramic acid which includes several improvements over published methods, especially with regard to purification procedures. The synthetic strategy is applicable for the synthesis of further Mur ligase substrates. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.098
• 作为产物：
  描述：

  p-nitrophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 在 salmonella chitinase 作用下， 反应 3.33h， 生成 2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖
  参考文献：
  名称：

  新型鼠伤寒沙门氏菌几丁质酶的表征，该酶水解几丁质，壳寡糖和N-乙酰基乳糖胺共轭物

  摘要：

  沙门氏菌含有注释为几丁质酶的基因。然而，它们的几丁质分解活性从未得到证实。现在，我们证明了针对分配给鼠伤寒沙门氏菌SL1344中SL0018（chiA）基因编码的糖苷水解酶家族18的几丁质酶的这种活性。通过PCR扩增缺乏假定的几丁质结合域的chiA的C末端截短形式，克隆并在具有N末端（His）6标签的大肠杆菌BL21（DE3）中表达。纯化的酶水解4-硝基苯基N，N'-二乙酰基-β- d-壳聚糖，4-硝基苯基β- d - N，Ñ '，Ñ “-triacetylchitotriose和羧甲基甲壳素雷玛唑亮紫但不作用4-硝基苯基ñ -乙酰基β- d -glucosaminide，肽聚糖或4-硝基苯基β- d -cellobioside。酶活性的特征还在于使用1 H核磁共振直接监测产物的形成，这表明几丁质是释放N，N'-二乙酰基壳二糖的底物。水解在保留构型的情况下发生，并且该酶仅作用于壳寡糖底物的

  DOI：

  10.1093/glycob/cwq174
• 作为试剂：
  描述：

  4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside 在 2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 、 hen eggwhite (HEW) lysozyme 、 水 作用下， 反应 2.0h， 生成 羟甲香豆素
  参考文献：
  名称：

  Hydrolysis of 4-methylumbelliferyl tetra-N-acetyl-.BETA.-chitotetraoside by lysozyme and its inhibition by N,N',N"-triacetylchitotriose.

  摘要：

  溶菌酶对4-甲基伞形酮四-N-乙酰-β-壳四糖(4-MU-(GlcNAc)4)的水解活性受离子强度的影响很小,尽管溶菌酶对微球菌悬浮液的水解活性随离子强度的变化而有显著差异。0.1mM的N, N', N"-三乙酰壳三糖((GlcNAc)3)抑制了溶菌酶对4-MU-(GlcNAc)4作为底物的40-60%活性,但溶菌酶对微球菌的溶解活性影响不大。研究了鸡蛋清(HEW)溶菌酶和人胎盘(HP)溶菌酶对4-MU-(GlcNAc)4的水解动力学以及(GlcNAc)3对此水解的抑制作用。HEW溶菌酶和HP溶菌酶对4-MU-(GlcNAc)4的K5值分别为19.7μM和27.9μM,而Vmax值分别为0.124和0.0833 nmol/min/mg。两种酶的k值都很低,暗示底物分子中的切割键相对于溶菌酶活性位点的取向不佳。(GlcNAc)3以双曲线混合型抑制作用抑制溶菌酶。抑制作用降低了两种溶菌酶的Vmax值。加入抑制剂后,HEW溶菌酶的K5值增加,而HP溶菌酶的K5值降低。HEW溶菌酶和HP溶菌酶的Ki值分别为29.6μM和106μM。

  DOI：

  10.1248/cpb.32.3607

文献信息

• PHOSPHORAMIDITE BUILDING BLOCKS FOR SUGAR-CONJUGATED OLIGONUCLEOTIDES
  申请人：AM CHEMICALS LLC

  公开号：US20160083414A1

  公开（公告）日：2016-03-24

  Novel nucleoside phosphoramidite building blocks for preparation of synthetic oligonucleotides containing at least one phosphotriester linkage conjugated to a monosaccharide and synthetic processes for making the same are disclosed. Furthermore, oligomeric compounds are prepared using said building blocks, preferably followed by removal of protecting groups to provide monosaccharide-conjugated oligonucleotides.

  揭示了用于制备含至少一种磷酸三酯键连接的寡核苷酸的合成寡核苷酸的新型核苷酸磷酰胺酯构建模块，其与单糖偶联，并公开了制备这些构建模块的合成过程。此外，使用这些构建模块制备寡聚合物化合物，最好是在去除保护基之后，以提供单糖偶联的寡核苷酸。
• [EN] IMIDAZOLIUM REAGENT FOR MASS SPECTROMETRY<br/>[FR] RÉACTIF D'IMIDAZOLIUM POUR SPECTROMÉTRIE DE MASSE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021234004A1

  公开（公告）日：2021-11-25

  The present invention relates to compounds which are suitable to be used in mass spectrometry as well as methods of mass spectrometric determination of analyte molecules using said compounds.

  本发明涉及适用于质谱的化合物，以及利用该化合物进行分析物分子的质谱测定方法。
• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
  申请人：Academia Sinica

  公开号：US20160102116A1

  公开（公告）日：2016-04-14

  Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.

  糖脂类脂质（GSLs）的组成和诱导化学因子独立于iNKT的方法被揭示。
• INTRACELLULAR SUBSTANCE TRANSPORT SYSTEM AND USE THEREOF
  申请人：National University Corporation Hokkaido University

  公开号：US20200138973A1

  公开（公告）日：2020-05-07

  The present invention pertains to a complex including nanoparticles and, carried on the surface of the nanoparticles, a lysosomal enzyme inhibitor or kinase inhibitor shown by general formula (A) and a phospholipid mimetic substance shown by general formula (B). In general formula (A), n1 is an integer of 2-30, n2 is an integer of 2-30, the -S- terminal is a nanoparticle-carrying site, and R10 is a suicide substrate site or a kinase inhibition site. In general formula (B), n3 is an integer in the range of 2-30, and the -S- terminal is a nanoparticle-carrying site. The present invention provides a versatile system capable of efficiently delivering a drug to endolysosomes and allowing the drug to function at a low concentration on lysosomal enzymes, and an anticancer agent in which this system is used.

  本发明涉及一种包括纳米粒子的复合物，所述纳米粒子表面携带有一种由通用式（A）显示的溶酶体酶抑制剂或激酶抑制剂以及一种由通用式（B）显示的磷脂类拟物物质。 在通用式（A）中，n1是2-30的整数，n2是2-30的整数，-S-端是纳米粒子携带位点，R10是自杀底物位点或激酶抑制位点。在通用式（B）中，n3是2-30范围内的整数，-S-端是纳米粒子携带位点。本发明提供了一种多功能系统，能够有效地将药物传递至内溶酶体，并使药物在低浓度下对溶酶体酶起作用，以及使用该系统的抗癌剂。
• CHITOSAN COVALENTLY LINKED WITH SMALL MOLECULE INTEGRIN ANTAGONIST FOR TARGETED DELIVERY
  申请人：Hoffmann-La Roche Inc.

  公开号：US20130197205A1

  公开（公告）日：2013-08-01

  The invention relates to the chitosan polymer derivatives of formula I: and pharmaceutically acceptable salts and esters thereof, wherein Y, X 1 , X 4 , R1, R2, and n are defined in the detailed description and claims. The chitosan polymer derivatives of formula I bind to or associate with alpha-4-beta-1 (α4β1) and alpha-V-beta-3 (αVβ3) integrin dimers and can be used in delivery formulations to deliver drugs, nucleic acids, or other therapeutic compounds to tissues or cells expressing such integrins.

  该发明涉及公式I的壳聚糖聚合物衍生物： 及其药用可接受的盐和酯，其中Y、X 1 、X 4 、R1、R2和n在详细说明和权利要求中有定义。公式I的壳聚糖聚合物衍生物与α4β1和αVβ3整合素二聚体结合或结合，并可用于传递制剂以将药物、核酸或其他治疗化合物传递到表达这些整合素的组织或细胞中。

表征谱图