Carbohydrate Research p. 755 - 763 (2000)
Update date:2022-08-03
Topics:
Kasuya, Maria Carmelita Z
Wang, Lai X
Lee, Yuan C
Mitsuki, Motoaki
Nakajima, Hideki
Miura, Yoshiaki
Sato, Toshinori
Hatanaka, Kenichi
Yamagata, Sadako
Yamagata, Tatsuya
A lactoside primer, 12-azidododecyl β-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the β-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the ω-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired ω-azidododecyl β-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated ω-azidododecyl β-lactoside primer was 75% of the amount of sialylated n-dodecyl β-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the ω-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides.
View MoreShanghai Synmedia Chemical Co., Ltd
Contact:+86-21-38681880
Address:6th Floor, 11A Building, No.528 Ruiqing Road, Heqing town, Pudong new district, Shanghai China
Contact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
Contact:86-311-83160559
Address:shijiazhuang
Disynthesis Chemical Technology Co. Ltd.
Contact:+86-571-88194596
Address:Dengyun road 380, Gongshu district, Hangzhou city, China
Contact:
Address:308# dongwu avenue dongxihu district wuhan city
Doi:10.1002/cbic.200900600
(2010)Doi:10.1016/j.jorganchem.2010.12.030
(2011)Doi:10.1021/om00047a007
(1991)Doi:10.1055/s-0030-1259512
(2011)Doi:10.1021/ja00001a037
(1991)Doi:10.1039/c1cc10438a
(2011)