一种用于Fmoc固相肽合成的胺衍生化、负载DOTA的聚合物载体。
An amine-derivatized, DOTA-loaded polymeric support for Fmoc Solid Phase Peptide Synthesis.
作者信息
Yoo Byunghee, Sheth Vipul R, Pagel Mark D
机构信息
Biomedical Engineering Interdisciplinary Program, The University of Arizona, Tucson AZ.
出版信息
Tetrahedron Lett. 2009 Aug 5;50(31):4459-4462. doi: 10.1016/j.tetlet.2009.05.061.
Abstract
An amine-derivatized DOTA has been used to modify the surface of a polymeric support for conventional Solid Phase Peptide Synthesis (SPPS) following standard Fmoc chemistry methods. This methodology was used to synthesize a peptide-DOTA conjugate that was demonstrated to be a PARACEST MRI contrast agent. Therefore, this synthesis methodology can facilitate Fmoc SPPS of molecular imaging contrast agents.
摘要
一种胺衍生化的DOTA已被用于按照标准的Fmoc化学方法修饰用于传统固相肽合成（SPPS）的聚合物载体表面。该方法用于合成一种肽-DOTA缀合物，已证明其为一种PARACEST MRI造影剂。因此，这种合成方法可促进分子成像造影剂的Fmoc SPPS。
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1
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Org Biomol Chem. 2008 Mar 7;6(5):815-28. doi: 10.1039/b718157b. Epub 2008 Feb 1.
2
The synthesis and chelation chemistry of DOTA-peptide conjugates.DOTA-肽缀合物的合成与螯合化学
Bioconjug Chem. 2008 Feb;19(2):391-402. doi: 10.1021/bc700328s. Epub 2007 Dec 12.
3
From combinatorial chemistry to cancer-targeting peptides.从组合化学到癌症靶向肽。
Mol Pharm. 2007 Sep-Oct;4(5):631-51. doi: 10.1021/mp700073y. Epub 2007 Sep 20.
4
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5
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J Am Chem Soc. 2006 Nov 1;128(43):14032-3. doi: 10.1021/ja063874f.
6
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Biopolymers. 2004;76(5):391-403. doi: 10.1002/bip.20139.
7
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8
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10
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Genes Dev. 2003 Mar 1;17(5):545-80. doi: 10.1101/gad.1047403.
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