用于通过化学选择性酰胺连接合成β-寡肽的对映体纯异恶唑烷酮单体的不对称合成。
Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β-oligopeptides by chemoselective amide ligation.
作者信息
Juarez-Garcia M Elisa, Yu Shouyun, Bode Jeffrey W
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6354, USA.
出版信息
Tetrahedron. 2010 Jun 26;66(26):4841-4853. doi: 10.1016/j.tet.2010.04.016.
Abstract
The design and general synthesis of enantiopure isoxazolidinone monomers as precursors for the preparation of enantiopure N-terminal hydroxylamine-β(3)-oligopeptides, which may be used as reaction partners with α-ketoacids in the decarboxylative amide ligation reaction, is described.
摘要
描述了对映体纯的异恶唑烷酮单体的设计与一般合成方法，这些单体作为前体用于制备对映体纯的N-末端羟胺-β(3)-寡肽，该寡肽可在脱羧酰胺连接反应中作为与α-酮酸的反应伙伴。
相似文献
1
Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β-oligopeptides by chemoselective amide ligation.
Tetrahedron. 2010 Jun 26;66(26):4841-4853. doi: 10.1016/j.tet.2010.04.016.
2
Iterative, aqueous synthesis of beta3-oligopeptides without coupling reagents.
J Am Chem Soc. 2006 Feb 8;128(5):1452-3. doi: 10.1021/ja057706j.
3
Synthesis of an enantiopure isoxazolidine monomer for β-aspartic acid in chemoselective β-oligopeptide synthesis.
Tetrahedron Lett. 2009 Jul 1;50(26):3258-3260. doi: 10.1016/j.tetlet.2009.02.045.
4
Traceless preparation of C-terminal α-ketoacids for chemical protein synthesis by α-ketoacid-hydroxylamine ligation: synthesis of SUMO2/3.
Angew Chem Int Ed Engl. 2014 Nov 3;53(45):12248-52. doi: 10.1002/anie.201407014. Epub 2014 Sep 22.
5
Chemical Protein Synthesis with the α-Ketoacid-Hydroxylamine Ligation.
Acc Chem Res. 2017 Sep 19;50(9):2104-2115. doi: 10.1021/acs.accounts.7b00277. Epub 2017 Aug 29.
6
Chemical Protein Synthesis by Chemoselective #x03B1;-Ketoacid-Hydroxylamine (KAHA) Ligations with 5-Oxaproline.
Methods Mol Biol. 2021;2355:151-162. doi: 10.1007/978-1-0716-1617-8_14.
7
Nitrone protecting groups for enantiopure N-hydroxyamino acids: synthesis of N-terminal peptide hydroxylamines for chemoselective ligations.
Org Biomol Chem. 2010 Aug 7;8(15):3405-17. doi: 10.1039/c004490c. Epub 2010 Jun 22.
8
Chemoselective protection of alpha-ketoacids by direct annulations with oximes.
Org Lett. 2010 May 7;12(9):1924-7. doi: 10.1021/ol100467t.
9
Chemical Protein Synthesis with the KAHA Ligation.
Top Curr Chem. 2015;363:1-31. doi: 10.1007/128_2014_597.
10
Mechanistic Insight into the TBHP-Mediated Decarboxylative Condensation of α-Ketoacids: Reaction Development and Application to Oligopeptide Synthesis.
Chem Pharm Bull (Tokyo). 2023;71(5):354-359. doi: 10.1248/cpb.c22-00910.
引用本文的文献
1
Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation.
Beilstein J Org Chem. 2021 Nov 24;17:2781-2786. doi: 10.3762/bjoc.17.188. eCollection 2021.
2
Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate.
Molecules. 2018 Jun 13;23(6):1440. doi: 10.3390/molecules23061440.
3
Synthetic fermentation of bioactive non-ribosomal peptides without organisms, enzymes or reagents.
Nat Chem. 2014 Oct;6(10):877-84. doi: 10.1038/nchem.2048. Epub 2014 Sep 7.
本文引用的文献
1
A general strategy for the preparation of C-terminal peptide alpha-ketoacids by solid phase peptide synthesis.
Org Biomol Chem. 2009 Jun 7;7(11):2259-64. doi: 10.1039/b901198f. Epub 2009 Apr 2.
2
Inhibition of gamma-secretase activity by helical beta-peptide foldamers.
J Am Chem Soc. 2009 Jun 3;131(21):7353-9. doi: 10.1021/ja9001458.
3
A rationally designed aldolase foldamer.
Angew Chem Int Ed Engl. 2009;48(5):922-5. doi: 10.1002/anie.200804996.
4
Chemoselective ligation and modification strategies for peptides and proteins.
Angew Chem Int Ed Engl. 2008;47(52):10030-74. doi: 10.1002/anie.200801313.
5
Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide alpha-ketoacids.
J Am Chem Soc. 2008 Apr 2;130(13):4253-5. doi: 10.1021/ja800053t. Epub 2008 Mar 12.
6
Toward beta-amino acid proteins: design, synthesis, and characterization of a fifteen kilodalton beta-peptide tetramer.
J Am Chem Soc. 2008 Jan 23;130(3):821-3. doi: 10.1021/ja077245x. Epub 2008 Jan 1.
7
Foldamers as versatile frameworks for the design and evolution of function.
Nat Chem Biol. 2007 May;3(5):252-62. doi: 10.1038/nchembio876.
8
Biophysical characterization of a beta-peptide bundle: comparison to natural proteins.
J Am Chem Soc. 2007 May 2;129(17):5344-5. doi: 10.1021/ja070567g. Epub 2007 Apr 11.
9
Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids.
Chem Commun (Camb). 2007 Feb 28(8):849-51. doi: 10.1039/b613410f. Epub 2006 Nov 23.
10
High-resolution structure of a beta-peptide bundle.
J Am Chem Soc. 2007 Feb 14;129(6):1532-3. doi: 10.1021/ja068678n.
Zotero 插件