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通过化学方法构建“生物”水平结构：单分子五价MUC1糖肽构建体的全合成。

"Biologic" level structures through chemistry: A total synthesis of a unimolecular pentavalent MUCI glycopeptide construct.

作者信息

Lee Dongjoo, 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 Lett. 2009 May 13;50(19):2167-2170. doi: 10.1016/j.tetlet.2009.02.138.

DOI:10.1016/j.tetlet.2009.02.138
PMID:21423786
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3059311/
Abstract

A convergent synthesis of a unimolecular pentavalent-MUC1 glycopeptide has been accomplished. A tandem repeat of unglycosylated human tumor-associated MUC1, a potential target for cancer immunotherapy, was incorporated into the known unimolecular pentavalent carbohydrate construct (5). This is an important step towards the development of a new fully synthetic anti-cancer vaccine candidate (1).

摘要

已完成一种单分子五价-MUC1糖肽的汇聚合成。未糖基化的人肿瘤相关MUC1的串联重复序列（癌症免疫治疗的一个潜在靶点）被纳入已知的单分子五价碳水化合物构建体（5）中。这是朝着开发一种全新的全合成抗癌疫苗候选物迈出的重要一步（1）。

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Tetrahedron Lett. 2009 May 13;50(19):2167-2170. doi: 10.1016/j.tetlet.2009.02.138.
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Recent Development in Carbohydrate Based Anti-cancer Vaccines.基于碳水化合物的抗癌疫苗的最新进展。
J Carbohydr Chem. 2012;31(3):143-186. doi: 10.1080/07328303.2012.659364. Epub 2012 Feb 29.
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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.

本文引用的文献

1
Preparation and evaluation of unimolecular pentavalent and hexavalent antigenic constructs targeting prostate and breast cancer: a synthetic route to anticancer vaccine candidates.靶向前列腺癌和乳腺癌的单分子五价和六价抗原构建体的制备与评估：抗癌疫苗候选物的合成途径
J Am Chem Soc. 2006 Mar 1;128(8):2715-25. doi: 10.1021/ja057244+.
2
Synthetic carbohydrate-based antitumor vaccines: challenges and opportunities.基于合成碳水化合物的抗肿瘤疫苗：挑战与机遇
Expert Rev Vaccines. 2005 Oct;4(5):677-85. doi: 10.1586/14760584.4.5.677.
3
Randomized phase IIB trial of BLP25 liposome vaccine in stage IIIB and IV non-small-cell lung cancer.BLP25脂质体疫苗用于IIIB期和IV期非小细胞肺癌的随机IIB期试验。
J Clin Oncol. 2005 Sep 20;23(27):6674-81. doi: 10.1200/JCO.2005.13.011.
4
Carbohydrate vaccines as immunotherapy for cancer.碳水化合物疫苗作为癌症免疫疗法
Immunol Cell Biol. 2005 Aug;83(4):418-28. doi: 10.1111/j.1440-1711.2005.01350.x.
5
Organic synthesis in pursuit of immunology: large-scale synthesis of peracetylated GM2 glycosylamino acid for preparation of a multiantigenic prostate cancer vaccine.追求免疫学的有机合成：用于制备多抗原性前列腺癌疫苗的全乙酰化GM2糖基氨基酸的大规模合成。
Bioorg Med Chem. 2005 Sep 1;13(17):5259-66. doi: 10.1016/j.bmc.2005.06.018.
6
Vaccination of patients with small-cell lung cancer with synthetic fucosyl GM-1 conjugated to keyhole limpet hemocyanin.用与钥孔戚血蓝蛋白偶联的合成岩藻糖基GM-1对小细胞肺癌患者进行疫苗接种。
Clin Cancer Res. 2004 Sep 15;10(18 Pt 1):6094-100. doi: 10.1158/1078-0432.CCR-04-0482.
7
Prospects for total synthesis: a vision for a totally synthetic vaccine targeting epithelial tumors.全合成的前景：针对上皮肿瘤的全合成疫苗的设想。
Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):11937-42. doi: 10.1073/pnas.0401894101. Epub 2004 Jul 27.
8
On the power of chemical synthesis: immunological evaluation of models for multiantigenic carbohydrate-based cancer vaccines.论化学合成的力量：基于多抗原碳水化合物的癌症疫苗模型的免疫学评估
Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13699-704. doi: 10.1073/pnas.202427599. Epub 2002 Oct 1.
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Pursuit of optimal carbohydrate-based anticancer vaccines: preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewis(y) antigens.追求基于碳水化合物的最佳抗癌疫苗：制备一种包含Tn、MBr1和Lewis(y)抗原的多抗原单分子糖肽。
J Am Chem Soc. 2001 Mar 7;123(9):1890-7. doi: 10.1021/ja002779i.
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Immunization of metastatic breast cancer patients with a fully synthetic globo H conjugate: a phase I trial.用全合成的人乳脂肪球膜糖脂H缀合物对转移性乳腺癌患者进行免疫治疗：一项I期试验。
Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3270-5. doi: 10.1073/pnas.051626298.