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Synthesis of β-d-glucopyranuronosylamine in aqueous solution : kinetic study and synthetic potential

หน่วยงาน Nanyang Technological University, Singapore

รายละเอียด

ชื่อเรื่อง : Synthesis of β-d-glucopyranuronosylamine in aqueous solution : kinetic study and synthetic potential
นักวิจัย : Ghadban, Ali , Albertin, Luca , Mounguengui, Rédéo W. Moussavou , Peruchon, Alexandre , Heyraud, Alain
คำค้น : DRNTU::Engineering::Materials::Composite materials , DRNTU::Science::Biological sciences
หน่วยงาน : Nanyang Technological University, Singapore
ผู้ร่วมงาน : -
ปีพิมพ์ : 2554
อ้างอิง : Ghadban, A., Albertin, L., Mounguengui, R. W. M., Peruchon, A. & Heyraud, A. 2011. Synthesis of β-d-glucopyranuronosylamine in aqueous solution: kinetic study and synthetic potential. Carbohydrate Research, 346(15), 2384 - 2393. , http://hdl.handle.net/10220/19506 , http://dx.doi.org/10.1016/j.carres.2011.08.018
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : Carbohydrate research
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

A systematic study of the synthesis of β-d-glucopyranuronosylamine in water is reported. When sodium d-glucuronate was reacted with ammonia and/or volatile ammonium salts in water a mixture of β-d-glucopyranuronosylamine and ammonium N-β-d-glucopyranuronosyl carbamate was obtained at a rate that strongly depended on the experimental conditions. In general higher ammonia and/or ammonium salt concentrations led to a faster conversion of the starting sugar into intermediate species and of the latter into the final products. Yet, some interesting trends and exceptions were observed. The use of saturated ammonium carbamate led to the fastest rates and the highest final yields of β-d-glucopyranuronosylamine/carbamate. With the exception of 1 M ammonia and 0.6 M ammonium salt, after 24 h of reaction all tested protocols led to higher yields of β-glycosylamine/carbamate than concentrated commercial ammonia alone. The mole fraction of α-d-glucopyranuronosylamine/carbamate at equilibrium was found to be 7–8% in water at 30 °C. Concerning bis(β-d-glucopyranuronosyl)amine, less than 3% of it is formed in all cases, with a minimum value of 0.5% in the case of saturated ammonium carbamate. Surprisingly, the reaction was consistently faster in the case of sodium d-glucuronate than in the case of d-glucose (4–8 times faster). Finally, the synthetic usefulness of our approach was demonstrated by the synthesis of three N-acyl-β-d-glucopyranuronosylamines and one N-alkylcarbamoyl-β-d-glucopyranuronosylamine directly in aqueous–organic solution without resorting to protective group chemistry.

บรรณานุกรม :
Ghadban, Ali , Albertin, Luca , Mounguengui, Rédéo W. Moussavou , Peruchon, Alexandre , Heyraud, Alain . (2554). Synthesis of β-d-glucopyranuronosylamine in aqueous solution : kinetic study and synthetic potential.
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Ghadban, Ali , Albertin, Luca , Mounguengui, Rédéo W. Moussavou , Peruchon, Alexandre , Heyraud, Alain . 2554. "Synthesis of β-d-glucopyranuronosylamine in aqueous solution : kinetic study and synthetic potential".
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Ghadban, Ali , Albertin, Luca , Mounguengui, Rédéo W. Moussavou , Peruchon, Alexandre , Heyraud, Alain . "Synthesis of β-d-glucopyranuronosylamine in aqueous solution : kinetic study and synthetic potential."
    กรุงเทพมหานคร : Nanyang Technological University, Singapore, 2554. Print.
Ghadban, Ali , Albertin, Luca , Mounguengui, Rédéo W. Moussavou , Peruchon, Alexandre , Heyraud, Alain . Synthesis of β-d-glucopyranuronosylamine in aqueous solution : kinetic study and synthetic potential. กรุงเทพมหานคร : Nanyang Technological University, Singapore; 2554.