乙烯型β-氨基酸的不对称合成及其在混合主链低聚物中的掺入。
Asymmetric synthesis of vinylogous β-amino acids and their incorporation into mixed backbone oligomers.
作者信息
Wu Hao, An Hongchan, Mo Shuting Cynthia, Kodadek Thomas
机构信息
Department of Chemistry, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL 33458, USA.
出版信息
Org Biomol Chem. 2017 Apr 11;15(15):3255-3264. doi: 10.1039/c7ob00333a.
Abstract
Chiral vinylogous β-amino acids (VBAA) were synthesized using enantioselective Mannich reactions of aldehydes with in situ generated N-carbamoyl imines followed by a Horner-Wadsworth-Emmons reaction. The efficiency with which these units could be incorporated into oligomers with different moieties on the C- and N-terminal sides was established, as was the feasibility of sequencing oligomers containing VBAAs by tandem mass spectrometry. The data show that VBAAs will be useful building blocks for the construction of combinatorial libraries of peptidomimetic compounds.
摘要
通过醛与原位生成的N-甲酰基亚胺的对映选择性曼尼希反应，随后进行霍纳-沃兹沃思-埃蒙斯反应，合成了手性乙烯基β-氨基酸（VBAA）。确定了这些单元能够以何种效率并入C端和N端带有不同部分的低聚物中，以及通过串联质谱对含有VBAA的低聚物进行测序的可行性。数据表明，VBAA将成为构建拟肽化合物组合文库的有用构件。
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