Journal of the American Chemical Society p. 5972 - 5976 (1992)
Update date:2022-08-11
Topics:
Pouyani, Tara
Kuo, Jing-Wen
Harbison, Gerard S.
Prestwich, Glenn D.
Hyaluronic acid (HA) is a naturally-occurring linear polysaccharide consisting of alternating D-glucuronic acid and N-acetyl-D-glucosamine residues. Reaction of the carboxyl group of the glucuronate residues with l-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDC) in the presence of primary amines yielded only the N-acylurea adducts rather than the expected amide coupling products. To determine the nature of this linkage unambiguously and to deduce the primary structure of the N-acylurea products, 13C- and 15N-labeled l-ethyl-3-(3-(dimethylamino)propyl)carbodiimide were synthesized. The isotopically-labeled carbodiimides were coupled to the carboxyl group of HA (molecular size ca. 2 000 000 Da) in water at pH = 4.75. The modified polysaccharides were then isolated, purified, and examined by cross polarization and magic angle spinning (CP-MAS) solid-state 13C and 15N NMR. The chemical shifts and states of protonation of the nitrogens confirmed the presence of two isomeric N-acylureas in unequal amounts and ruled out the presence of any unrearranged O-acylurea product.
View Morewebsite:http://www.herbpurify.com
Contact:0086-028-85249238
Address:Room709-C1,Incubator Building, Tianfu Life Science Park No.88,Keyuan Road,Gaoxin district,Chengdu City,Sichuan Prov,China
Guilin Zhenda Bio-Tech Co., Ltd.
Contact:86-773-3568977
Address:-Yangtang shangshui industry park, Lingui county,
Contact:+86-633-8332928
Address:No.1,Huanghai Yilu.Rizhao,Shandong
Beyond Pharmaceutical Co., Ltd
Contact:+86-571-8195-3185
Address:No. 13-1, Liansheng Road, Yuhang District
Compro Shijiazhuang Fine Chemical Co., Ltd
Contact:0086-311-89689838
Address:Economic and Technological Development Zone of Shijiazhuang,Hebei
Doi:10.1016/j.orgel.2020.105899
(2020)Doi:10.1002/prac.19923340314
(1992)Doi:10.1039/c3gc40789f
(2013)Doi:10.1021/bm900896h
(2010)Doi:10.1016/j.biopha.2016.06.008
(2016)Doi:10.1021/jo00073a018
(1993)