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人促甲状腺激素(hTSH)β亚基的全化学合成:精氨酸标记的乙酰氨基甲基(Acm)保护基的应用

Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH) -Subunit: Application of Arginine-tagged Acetamidomethyl (Acm) Protecting Groups.

作者信息

Brailsford John A, Stockdill Jennifer L, Axelrod Abram J, Peterson Michael T, Vadola Paul A, Johnston Eric V, Danishefsky Samuel J

机构信息

Laboratory for Bioorganic Chemistry, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, NY 10065.

出版信息

Tetrahedron. 2018 Apr 12;74(15):1951-1956. doi: 10.1016/j.tet.2018.02.067. Epub 2018 Mar 6.

DOI:10.1016/j.tet.2018.02.067
PMID:30853725
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6402344/
Abstract

The β-subunit of human thyroid stimulating hormone (hTSH) has been synthesized as a single glycoform bearing a chitobiose disaccharide at the native glycosylation site. Key to the successful completion of this synthesis was the introduction of an arginine-tagged acetamidomethyl group, which served to greatly facilitate handling of a glycopeptide fragment with poor aqueous solubility. This general solution to the challenge of working with intractable peptides is expected to find wide use in protein synthesis.

摘要

人促甲状腺激素(hTSH)的β亚基已被合成为一种单一糖型,在天然糖基化位点带有一个壳二糖二糖。成功完成该合成的关键是引入了一个带有精氨酸标签的乙酰氨基甲基基团,这极大地便于处理水溶性差的糖肽片段。这种应对难处理肽挑战的通用解决方案有望在蛋白质合成中得到广泛应用。

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Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH) -Subunit: Application of Arginine-tagged Acetamidomethyl (Acm) Protecting Groups.人促甲状腺激素(hTSH)β亚基的全化学合成:精氨酸标记的乙酰氨基甲基(Acm)保护基的应用
Tetrahedron. 2018 Apr 12;74(15):1951-1956. doi: 10.1016/j.tet.2018.02.067. Epub 2018 Mar 6.
2
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Substitution of the seat-belt region of the thyroid-stimulating hormone (TSH) beta-subunit with the corresponding regions of choriogonadotropin or follitropin confers luteotropic but not follitropic activity to chimeric TSH.用绒毛膜促性腺激素或促卵泡激素的相应区域替换促甲状腺激素(TSH)β亚基的安全带区域,可赋予嵌合TSH促黄体生成活性,但不赋予促卵泡生成活性。
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An iodine-free and directed-disulfide-bond-forming route to insulin analogues.无碘且定向形成二硫键的胰岛素类似物合成途径。
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Chemical synthesis of the β-subunit of human luteinizing (hLH) and chorionic gonadotropin (hCG) glycoprotein hormones.人促黄体生成素(hLH)和绒毛膜促性腺激素(hCG)糖蛋白激素β亚基的化学合成。
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一种克服天然化学连接中使用的N端半胱氨酰肽段溶解性挑战的直接方法。
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Challenges and Perspectives in Chemical Synthesis of Highly Hydrophobic Peptides.高疏水性肽化学合成中的挑战与展望
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通过 Fmoc 化学方法快速全合成中小分子量的膜蛋白。
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Synthesis of autophagosomal marker protein LC3-II under detergent-free conditions.在无去污剂条件下自噬体标记蛋白LC3-II的合成。
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Eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group for the synthesis of Cys-containing peptides.固定化 PGA 酶和 S-Phacm 保护基的环保组合用于含半胱氨酸肽的合成。
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An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation.通过天冬氨酸酰化作用实现均相 N-连接糖肽的化学合成的进展。
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Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone.人糖蛋白激素α-亚基的全合成:向完全合成的均一人促卵泡激素迈进。
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