Regiospecific glycosidase-assisted synthesis of lacto-N-biose I (Galβ1-3GlcNAc) and 3′-sialyl-lacto-N-biose I (NeuAcα2-3Galβ1-3GlcNAc)
Regiospecific glycosidase-assisted synthesis of lacto-N-biose I (Galβ1-3GlcNAc) and 3′-sialyl-lacto-N-biose I (NeuAcα2-3Galβ1-3GlcNAc)
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DOI：
10.1046/j.1432-1327.2000.01068.x
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发表时间：
2000-02-01
期刊：
影响因子：
--
通讯作者：
Paoletti, S
中科院分区：
文献类型：
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作者：
Vetere, A;Miletich, M;Paoletti, S
进行乳-N-二糖I（Gal β 1-3GlcNAc）和3 '-唾液酸-乳-N-二糖I（NeuAc α 2-3Gal β 1-3GlcNAc）的全转糖酵解合成。以对硝基苯基β-D-吡喃半乳糖苷为供体，2-乙酰氨基-2-脱氧-D-吡喃葡萄糖为受体，木薯黄单胞菌β-D-半乳糖苷酶为催化剂，合成乳糖-N-二糖I。该反应显示出区域特异性，相对于供体具有高摩尔产率（约55%）。将通过该方法获得的乳糖-N-二糖I用作随后由克氏锥虫转唾液酸酶催化的酶促反应的受体，其中将2 ′-（4-甲基伞形酰）-α-D-N-乙酰神经氨酸用作N-乙酰神经氨酸部分的供体。反应区域特异性地产生产物3 '-唾液酸-乳糖-N-二糖I，摩尔产率约为35%。
The all-transglycolytic synthesis of lacto-N-biose I (Gal beta 1-3GlcNAc) and 3'-sialyl-lacto-N-biose I (NeuAc alpha 2-3Gal beta 1-3GlcNAc) was performed. The disaccharide lacto-N-biose I was obtained by use of p-nitrophenyl beta-D-galactopyranoside as the donor, 2-acetamido-2-deoxy-D-glucopyranose as the acceptor and Xanthomonas manihotis beta-D-galactosidase as the catalyst. The reaction was shown to be regiospecific, with a high molar yield (about 55%) with respect to the donor. Lacto-N-biose I obtained by this method was used as the acceptor for a subsequent enzymatic reaction catalyzed by Trypanosoma cruzi trans-sialidase in which 2'-(4-methylumbellyferyl)-alpha-D-N-acetylneuraminic was used as the donor of the N-acetylneuraminil moiety. The reaction generated the product, 3'-sialyl-lacto-N-biose I, regiospecifically and with a molar yield of about 35%.