Vetere A, Miletich M, Bosco M, Paoletti S
Department of Biochemistry, Biophysics and Macromolecular Chemistry, University of Trieste, Italy.
Eur J Biochem. 2000 Feb;267(4):942-9. doi: 10.1046/j.1432-1327.2000.01068.x.
The all-transglycolytic synthesis of lacto-N-biose I (Galbeta1-3GlcNAc) and 3'-sialyl-lacto-N-biose I (NeuAcalpha2-3Galbeta1-3GlcNAc) 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%.
进行了乳糖-N-二糖I（Galβ1-3GlcNAc）和3'-唾液酸乳糖-N-二糖I（NeuAcα2-3Galβ1-3GlcNAc）的全糖酵解合成。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，利用木薯黄单胞菌β-D-半乳糖苷酶作为催化剂，获得了二糖乳糖-N-二糖I。该反应具有区域特异性，相对于供体具有较高的摩尔产率（约55%）。通过这种方法获得的乳糖-N-二糖I用作后续由克氏锥虫转唾液酸酶催化的酶促反应的受体，其中2'-（4-甲基伞形酮基）-α-D-N-乙酰神经氨酸用作N-乙酰神经氨酸部分的供体。该反应区域特异性地生成了产物3'-唾液酸乳糖-N-二糖I，摩尔产率约为35%。
