一种粘蛋白型O-糖基化氨基酸β-Gal-(1→3)-[α-Neu5Ac-(2→6)]-α-GalNAc-(1→3)-丝氨酸的合成
Synthesis of a mucin-type O-glycosylated amino acid, beta-Gal-(1----3)-[alpha-Neu5Ac-(2----6)]-alpha-GalNAc-(1----3)- Ser.
作者信息
Iijima H, Ogawa T
机构信息
RIKEN Institute of Physical and Chemical Research, Saitama, Japan.
出版信息
Carbohydr Res. 1989 Feb 15;186(1):95-106. doi: 10.1016/0008-6215(89)84008-x.
Total synthesis of O-beta-D-galactopyranosyl-(1----3)-O-[(5-acetamido-3,5-dideoxy- D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2----6)]-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1----3 )-L- serine was achieved by use of the key glycosyl donor O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1----3)-O- [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galact o-2- nonulopyranosyl)onate-(2----6)]-4-O-acetyl-2-azido-2-deoxy-a lpha-D- galactopyranosyl trichloroacetimidate and the key glycosyl acceptor N-(benzyloxycarbonyl)-L- serine benzyl ester in a regiocontrolled way.
通过使用关键糖基供体O-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-(1→3)-O-[甲基(5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬糖醛酸)-(2→6)]-4-O-乙酰基-2-叠氮基-2-脱氧-α-D-吡喃半乳糖基三氯乙酰亚胺酯和关键糖基受体N-(苄氧羰基)-L-丝氨酸苄酯，以区域控制的方式实现了O-β-D-吡喃半乳糖基-(1→3)-O-[(5-乙酰氨基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬糖醛酸)-(2→6)]-O-(2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基)-(1→3)-L-丝氨酸的全合成。
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