肽和糖肽合成的最新进展。
Recent Departures in the Synthesis of Peptides and Glycopeptides.
作者信息
Kan Cindy, Danishefsky Samuel J
机构信息
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10065, USA.
出版信息
Tetrahedron. 2009 Nov 7;65(45):9047-9065. doi: 10.1016/j.tet.2009.09.032.
Abstract
In this account, we describe the results of a research program directed to the proposition that chemical synthesis can play a valuable role in identifying biologic level molecules worthy of pharma level development. We recount our journey towards the chemical synthesis of homogeneous erythropoietin, the challenges we encountered, and our efforts to address deficiencies in the current "state of the art" of glycopeptide synthesis. Here we describe new methods for the synthesis of glycopeptides that have emerged from the erythropoietin adventure, including the development of unique C-terminal acyl donors, novel amide bond forming methods, and new ligation and coupling strategies.
摘要
在本报告中，我们描述了一项研究计划的成果，该计划旨在验证化学合成在鉴定值得进行药物水平开发的生物级分子方面可发挥重要作用这一命题。我们讲述了我们在合成均一促红细胞生成素的化学合成过程中的历程、遇到的挑战，以及我们为弥补当前糖肽合成“技术水平”的不足所做的努力。在此，我们描述了从促红细胞生成素合成历程中涌现出的糖肽合成新方法，包括独特的C端酰基供体的开发、新型酰胺键形成方法以及新的连接和偶联策略。
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本文引用的文献
1
Toward homogeneous erythropoietin: fine tuning of the C-terminal acyl donor in the chemical synthesis of the Cys29-Gly77 glycopeptide domain.朝着均一性的促红细胞生成素迈进：在 Cys29-Gly77 糖肽结构域的化学合成中对 C 末端酰基供体进行精细调控。
J Am Chem Soc. 2009 Apr 22;131(15):5432-7. doi: 10.1021/ja808705v.
2
Synthetic carbohydrate-based anticancer vaccines: the Memorial Sloan-Kettering experience.基于合成碳水化合物的抗癌疫苗：纪念斯隆-凯特琳癌症中心的经验
Expert Rev Vaccines. 2009 Oct;8(10):1399-413. doi: 10.1586/erv.09.95.
3
Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.迈向具有双天线 N 连接十二糖的全合成均一性β-人卵泡刺激素（β-hFSH）。在天然连接位点合成带有壳二糖单元的β-hFSH。
J Am Chem Soc. 2009 Apr 29;131(16):5792-9. doi: 10.1021/ja809554x.
4
Toward homogeneous erythropoietin: non-NCL-based chemical synthesis of the Gln78-Arg166 glycopeptide domain.朝着同质性促红细胞生成素迈进：基于非 NCL 的 Gln78-Arg166 糖肽结构域的化学合成。
J Am Chem Soc. 2009 Apr 22;131(15):5424-31. doi: 10.1021/ja808704m.
5
Toward homogeneous erythropoietin: chemical synthesis of the Ala1-Gly28 glycopeptide domain by "alanine" ligation.朝着同型促红细胞生成素迈进：通过“丙氨酸”连接化学合成 Ala1-Gly28 糖肽结构域。
J Am Chem Soc. 2009 Apr 22;131(15):5438-43. doi: 10.1021/ja808707w.
6
Emerging methods for the production of homogeneous human glycoproteins.生产均质人糖蛋白的新兴方法。
Nat Chem Biol. 2009 Apr;5(4):206-15. doi: 10.1038/nchembio.148.
7
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8
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J Am Chem Soc. 2008 Nov 26;130(47):15814-6. doi: 10.1021/ja804993y.
9
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Angew Chem Int Ed Engl. 2008;47(44):8521-4. doi: 10.1002/anie.200803523.
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