Synthesis of sphere-type monodispersed oligosaccharide-polypeptide dendrimers
Synthesis of sphere-type monodispersed oligosaccharide-polypeptide dendrimers
复制标题
DOI：
10.1021/ma030021o
复制
发表时间：
2003-09-23
期刊：
影响因子：
5.5
通讯作者：
Uryu, T
中科院分区：
文献类型：
--
作者：
Baigude, H;Katsuraya, K;Uryu, T
合成了分子量分布均匀的球形全取代低聚糖-β-丙氨酸-聚赖氨酸树枝状大分子。以1，4-二氨基丁烷为引发剂核，N，N‘-二(叔丁氧基甲酰基)-L-赖氨酸为支化单元，合成了球形聚赖氨酸树枝状大分子。β-丙氨酸与第三代聚赖氨酸树枝状大分子结合形成第三代树枝状大分子，其表面有16个末端氨基。将麦芽糖、乳糖、纤维二糖、麦芽三糖或乳糖和麦芽糖的混合物通过还原胺化的方法连接到β-丙氨酸-聚赖氨酸树枝状支架表面，得到了一系列球形的低聚糖-β-丙氨酸-聚赖氨酸树枝状大分子。高产率地合成了含32个寡糖残基的低聚糖-β-丙氨酸-聚赖氨酸树枝状大分子。核磁共振和MALDI-TOF质量测量表明，低聚糖-多肽树枝状大分子呈单分散状态，其对纤维二糖、麦芽糖和乳糖的相对分子质量分别为13 418.36、13 472.50和13 507.28 g/m ol，表明低聚糖完全取代了氨基。
A sphere-type fully substituted oligosaccharide-beta-alanine-poly(lysine) dendrimer having a sharp molecular weight distribution was synthesized. Sphere-type poly(lysine) dendrimers were prepared using 1,4-diaminobutane as an initiator core and N,N'-bis(tert-butyloxycarbonyl)-L-lysine as a branching unit. beta-Alanine was bound to the poly(lysine) dendrimer generation 3 to form beta-alanine-poly(lysine) dendrimer generation 3, which has 16 terminal amino groups on its surface. A series of sphere-type oligosaccharide-beta-alanine-poly(lysine) dendrimers were obtained by binding such an oligosaccharide as maltose, lactose, cellobiose, maltotriose, or a mixture of lactose and maltose to the surface of the beta-alanine-poly(lysine) dendrimer scaffolding by reductive amination using the borane-pyridine complex. Oligosaccharide-beta-alanine-poly(lysine) dendrimers having 32 oligosaccharide residues were obtained in high yields. NMR and MALDI-TOF mass measurements revealed that the oligosaccharide-polypeptide dendrimers have a monodispersed molecular weight distribution, the molecular weight of which was 13 418.36, 13 472.50, and 13 507.28 g/mol for cellobiose, maltose, and lactose, respectively, indicating that a complete substitution of the amino group by the oligosaccharide occurred.