加巴喷丁杂合肽与生物共轭物。
Gabapentin hybrid peptides and bioconjugates.
作者信息
Lebedyeva Iryna O, Ostrov David A, Neubert John, Steel Peter J, Patel Kunal, Sileno Sean M, Goncalves Kevin, Ibrahim Mohamed A, Alamry Khalid A, Katritzky Alan R
机构信息
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
Department of Pathology, Immunology and Laboratory Medicine, University of Florida College of Medicine, Gainesville, FL 32611, USA.
出版信息
Bioorg Med Chem. 2014 Feb 15;22(4):1479-86. doi: 10.1016/j.bmc.2013.12.017. Epub 2013 Dec 12.
Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (L-Ala-Gbp, L-Val-Gbp, L-Ala-L-Phe-Gbp, Gly-L-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.
研究了克服加巴喷丁环化形成其γ-内酰胺倾向的加巴喷丁生物共轭物的合成方法。加巴喷丁通过其N端的N-酰化反应转化为二肽、三肽和四肽（L-丙氨酸-加巴喷丁、L-缬氨酸-加巴喷丁、L-丙氨酸-L-苯丙氨酸-加巴喷丁、甘氨酸-L-丙氨酸-β-丙氨酸-加巴喷丁）。羧基活化的Boc保护的加巴喷丁用于对小肽和激素进行N-、O-和S-酰化反应，以得到共轭物，这些共轭物也可以提供含有构象受限加巴喷丁单元的前药。
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