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Selective bi-directional amide bond cleavage of N-methylcysteinyl peptide

หน่วยงาน Nanyang Technological University, Singapore

รายละเอียด

ชื่อเรื่อง : Selective bi-directional amide bond cleavage of N-methylcysteinyl peptide
นักวิจัย : Qiu, Yibo , Hemu, Xinya , Liu, Ding Xiang , Tam, James P.
คำค้น : DRNTU::Science::Chemistry::Organic chemistry
หน่วยงาน : Nanyang Technological University, Singapore
ผู้ร่วมงาน : -
ปีพิมพ์ : 2557
อ้างอิง : Qiu, Y., Hemu, X., Liu, D. X., & Tam, J. P. (2014). Selective Bi-directional Amide Bond Cleavage of N-Methylcysteinyl Peptide. European Journal of Organic Chemistry, 2014(20), 4370-4380. , 1434-193X , http://hdl.handle.net/10220/20068 , http://dx.doi.org/10.1002/ejoc.201402261
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : European journal of organic chemistry
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

A selective bi-directional peptide bond cleavage mediated by N-methylcysteine (MeCys) in Xaa-MeCys-Yaa peptides (Xaa and Yaa, non-cysteine residues) leading to thioesters and thiolactones is described. Rate and product analyses showed that an Nα-amide bond cleavage occurred at the Xaa-MeCys bond by an N–S acyl shift to generate an Xaa-S-(MeCys-Yaa) thioester at pH 1–5, whereas under strongly acidic conditions of H0 = –5, the MeCys-Yaa bond underwent a Cα-amide bond cleavage via an oxazolone intermediate, which was trapped by thiocresol (TC) as an Xaa-MeCys-TC thioester. This thioester was then transformed into an Xaa-MeCys-β-thiolactone at pH 4–5. Replacing MeCys by a Cys residue did not result in significant bi-directional peptide bond cleavage, which suggests that N-methylation in a MeCys residue is important for the N–S acyl shift reaction and formation of oxazolone. The isomerization of amides and thioesters was successfully used to prepare cyclic peptides.

บรรณานุกรม :
Qiu, Yibo , Hemu, Xinya , Liu, Ding Xiang , Tam, James P. . (2557). Selective bi-directional amide bond cleavage of N-methylcysteinyl peptide.
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Qiu, Yibo , Hemu, Xinya , Liu, Ding Xiang , Tam, James P. . 2557. "Selective bi-directional amide bond cleavage of N-methylcysteinyl peptide".
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Qiu, Yibo , Hemu, Xinya , Liu, Ding Xiang , Tam, James P. . "Selective bi-directional amide bond cleavage of N-methylcysteinyl peptide."
    กรุงเทพมหานคร : Nanyang Technological University, Singapore, 2557. Print.
Qiu, Yibo , Hemu, Xinya , Liu, Ding Xiang , Tam, James P. . Selective bi-directional amide bond cleavage of N-methylcysteinyl peptide. กรุงเทพมหานคร : Nanyang Technological University, Singapore; 2557.