CAS: 80265-04-9; 4-Methylumbelliferyl-2-Acetamido-2-Deoxy-Alpha-D-Glucopyranoside

该化合物是一种合成基底基体,通常用于生物化学实验,特别是用于检测N-acetyl-D-glucosaminadase等酶,这种合成基体具有4-甲基丙烯酮(一种荧光标志),它是一种荧光标记,可以很容易地直观地显示酶活动.N-ethery-D/lucosaminide分子部分作为甘醇基体.在目标酶进行水解时,释放4-memyum-umliferone导致荧光素的可测量增长,使其成为研究和诊断应用的宝贵工具.该化合物通常在有机溶剂和水中溶解,其荧光特性可能受到pH和溶剂条件的影响.重要的是,在使用适当的安全规程处理该物质时,如同任何化学试剂一样,4-emumbelfilyN-Acetl-d-grosaminide是用于研究的酶学和分子生物学研究的关键化合物.

英文名称4-Methylumbelliferyl-2-Acetamido-2-Deoxy-Alpha-D-Glucopyranoside
中文名称4-甲基伞形酮-2-乙酰胺基-2-脱氧-α-D-吡喃葡萄糖苷
IUPAC名称N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3-yl)acetamide
其它别名Glcnac1-Alpha-4Mu; 4-Methylumbelliferyl-2-Acetamido-2-Deoxy-Alpha-D-Glucopyranoside; 4-Methyl-2-Oxo-2H-Chromen-7-Yl 2-(Acetylamino)-2-Deoxy-Alpha-D-Glucopyranoside; 4-Methyl-2-Oxo-2H-1-Benzopyran-7-Yl 2
CAS编号80265-04-9
MFCD编号:MFCD00036771
分子式:C18H21NO8分子量:379.36
产品CID: 1797680
产品分类生物化工 → 糖类化合物 → 单糖

相似结构搜索
InChIKey: QCTHLCFVVACBSA-FGTAOJJYSA-N
InChI=1S/C18H21NO8/c1-8-5-14(22)26-12-6-10(3-4-11(8)12)25-18-15(19-9(2)21)17(24)16(23)13(7-20)27-18/h3-6,13,15-18,20,23-24H,7H2,1-2H3,(H,19,21)/t13-,15-,16-,17-,18+/m1/s1
计算化学: 氢键受体数8.0氢键供体数4.0可旋转键数4.0

物理性质

熔点224-225 °C
沸点732.169 °C at 760 mmHg
闪点396.601 °C
密度1.48 g/cm3
pKa:12.87±0.70(预测)
PSA:138.46
LogP:-0.1852
溶解性DMSO (Slightly), Methanol (Slightly), Water (Slightly, Heated)
外观形态白色至淡黄色白色固体
储存条件密封干燥,2-8°C
产品应用该化合物用于SANFILIPPO B综合症.

MSDS等安全信息

警示词Warning
危险描述H302-H315-H319-H335-
防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338-
危险品标志Xi
安全声明22-26-36
危险类别码36/37/38

上下游产品

合成工艺路线路线简述

📜4-Methylumbelliferyl 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-α-D-Glucopyranoside置于sodium Methylate体系中,用甲醇,氯仿作为反应溶剂,化学反应 0.05H,以75%的收率获得产物4-甲基伞形酮-2-乙酸胺基-2-脱氧-α-D-吡喃葡糖苷
参考文献:4-Methylumbelliferyl 2-Acetamido-2-Deoxy-α-D-Glucopyranoside,A Fluorogenic Substrate For N-Acetyl-α-D-Glucos-Aminidase
标题:4-Methylumbelliferyl 2-Acetamido-2-Deoxy-α-D-Glucopyranoside,A Fluorogenic Substrate For N-Acetyl-α-D-Glucos-Aminidase
摘要:Condensation Of Dimeric 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Nitroso-Alpha-D-Glucopyranosyl Chloride With 4-Methylumbelliferone Gave Crystalline 4-Methylumbelliferyl 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Oximino-Alpha-D-Arabino-Hexopyranoside. Acetylation Of This Adduct,Reduction Of The Resulting Crude O-Acetyloxime With Borane In Oxolane,And Acetylation Gave The 3,4,6-Tri-O-Acetyl Derivative Of 4-Methylumbelliferyl 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranoside (1). A New Sensitive Assay Of N-Acetyl-Alpha-D-Glucosaminidase (Ec 3.2.1.50) Is Made Possible By Fluorometric Measurement Of 4-Methylumbelliferone Liberated By Enzymic Hydrolysis Of Glycoside 1. Such Assays Are Illustrated By Results Obtained With Enzyme Preparations From Pig Liver And Human-Blood Serum.
DOI:10.1016/s0008-6215(00)84698-4