N-Acetyl-D-Glucosamine

1. Introduction of 2-Acetamido-2-deoxy-D-glucose
With the EINECS registry number 231-368-2, 2-Acetamido-2-deoxy-D-glucose is also called 2-(acetylamino)-2-deoxy-D-glucose. What's more, 2-Acetamido-2-deoxy-D-glucose is a kind of white powder which can be used to treat osteoarthritis and rheumatoid arthritis.

2. Properties of 2-Acetamido-2-deoxy-D-glucose
(1)ACD/LogP: -2.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.68; (4)ACD/LogD (pH 7.4): -2.68; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 74.3 Å²; (13)Index of Refraction: 1.541; (14)Molar Refractivity: 48.89 cm³; (15)Molar Volume: 155.3 cm³; (16)Polarizability: 19.38 ×10^-24cm³; (17)Surface Tension: 69.6 dyne/cm; (18)Density: 1.423 g/cm³; (19)Flash Point: 338.7 °C; (20)Enthalpy of Vaporization: 107.73 kJ/mol; (21)Boiling Point: 636.4 °C at 760 mmHg; (22)Vapour Pressure: 7.12E-19 mmHg at 25°C.

3. Structure Descriptors of 2-Acetamido-2-deoxy-D-glucose
(1)SMILES: O=C[C@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO
(2)Std. InChI: InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1
(3)Std. InChIKey: MBLBDJOUHNCFQT-LXGUWJNJSA-N

4. Safety Information of 2-Acetamido-2-deoxy-D-glucose
Hazard Symbols:Xi
Risk Codes:
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Description:
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

5. Preparation of 2-Acetamido-2-deoxy-D-glucose
Several crude enzymes including cellelase Tv, hemicellulase and lipase, papain as well as exllulase Ac were examined for the effective production of 2-Acetamido-2-deoxy-D-glucose from amorphous α-chitin. Among the tested crude enzymes, cellulase Iv was found to be the most effective for directly degrading amorphous α-chitin to 2-Acetamido-2-deoxy-D-glucose. High yield of 2-Acetamido-2-deoxy-D-glucose was achieved by choosing the optimum hydrolytic conditons at PH 4.5 and 37°C. By gradually adding, in three tantamount cases, the amount of cellulase Tv amorphous α-chitin, the yield of 2-Acetamido-2-deoxy-D-glucose reach 55%.

6. Use of 2-Acetamido-2-deoxy-D-glucose
Uses of 2-Acetamido-2-deoxy-D-glucose can react with phenylmethanol to get N-(O¹-benzyl-a-D-glucopyranose-2-yl)-acetamide]. This reaction will need reagent BF₃*Et₂O. The reaction time is 6 hours by heating. The yield is about 47%.



7. Other details of 2-Acetamido-2-deoxy-D-glucose
When you are using 2-Acetamido-2-deoxy-D-glucose, please be cautious about it as the following:
2-Acetamido-2-deoxy-D-glucose is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.