callipeltin B的固相全合成及结构确证
Solid-phase total synthesis and structure proof of callipeltin B.
作者信息
Krishnamoorthy Ravi, Vazquez-Serrano Leslie D, Turk Jeffrey A, Kowalski Jennifer A, Benson Alan G, Breaux Nneka T, Lipton Mark A
机构信息
Department of Chemistry and Cancer Center, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
出版信息
J Am Chem Soc. 2006 Dec 6;128(48):15392-3. doi: 10.1021/ja0666250.
Abstract
The cytotoxic, cyclic heptadepsipeptide, natural product callipeltin B was synthesized on a solid-phase support in 15% overall yield. Comparison of the 1H NMR spectra of three synthetic isomers with those of callipeltin B confirmed the configurational reassignment of its threonine residues as d-allothreonine and the assignment of the configuration of its beta-methoxytyrosine residue as (2R,3R).
摘要
细胞毒性环状七肽天然产物callipeltin B在固相载体上合成，总产率为15%。将三种合成异构体的1H NMR光谱与callipeltin B的光谱进行比较，证实其苏氨酸残基的构型重新指定为d-别苏氨酸，其β-甲氧基酪氨酸残基的构型指定为(2R,3R)。
相似文献
1
Solid-phase total synthesis and structure proof of callipeltin B.callipeltin B的固相全合成及结构确证
J Am Chem Soc. 2006 Dec 6;128(48):15392-3. doi: 10.1021/ja0666250.
2
Solid-phase synthesis and configurational reassigment of callipeltin E. Implications for the structures of callipeltins A and B.Callipeltin E的固相合成与构型重新确定。对Callipeltins A和B结构的启示。
J Org Chem. 2006 Aug 18;71(17):6351-6. doi: 10.1021/jo060351h.
3
Cytotoxic evaluation of natural and synthetic callipeltins: a revision of cytotoxicity of callipeltin B.天然和合成卡里佩尔汀的细胞毒性评估：卡里佩尔汀B细胞毒性的修订
Biosci Biotechnol Biochem. 2016 Jun;80(6):1066-9. doi: 10.1080/09168451.2016.1148581. Epub 2016 Feb 29.
4
Solid-phase synthesis of callipeltin D. Stereochemical confirmation of the unnatural amino acid AGDHE.Callipeltin D的固相合成。非天然氨基酸AGDHE的立体化学确证。
Org Lett. 2005 Dec 22;7(26):5881-3. doi: 10.1021/ol052438f.
5
Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A.β-甲氧基酪氨酸所有立体异构体的简洁合成及Callipeltin A中残基绝对构型的测定。
Org Lett. 2005 Aug 4;7(16):3585-8. doi: 10.1021/ol0513600.
6
Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: proof of configurational assignment.3-羟基-2,4,6-三甲基庚酸四种非对映异构体的不对称合成：构型归属的证明
J Org Chem. 2003 Oct 3;68(20):7841-4. doi: 10.1021/jo034738l.
7
Total synthesis of callipeltin B and M, peptidyl marine natural products.肽基海洋天然产物Callipeltin B和M的全合成。
Org Lett. 2014 Aug 15;16(16):4324-7. doi: 10.1021/ol5020619. Epub 2014 Jul 31.
8
Synthesis of the unnatural amino acid AGDHE, a constituent of the cyclic depsipeptides callipeltins A and D.非天然氨基酸AGDHE的合成，AGDHE是环缩肽callipeltins A和D的组成成分。
Org Lett. 2002 Dec 12;4(25):4455-8. doi: 10.1021/ol0269852.
9
Total synthesis of the antifungal depsipeptide petriellin A.抗真菌脂肽化合物 petriellin A 的全合成。
J Org Chem. 2011 Aug 19;76(16):6686-93. doi: 10.1021/jo201017w. Epub 2011 Jul 19.
10
Synthesis and cytotoxicity of the depsipeptides analogues of callipeltin B.Callipeltin B 类似物的 depsipeptides 的合成及细胞毒性。
Bioorg Med Chem Lett. 2011 Aug 15;21(16):4865-8. doi: 10.1016/j.bmcl.2011.06.026. Epub 2011 Jul 7.
引用本文的文献
1
Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Sponge.谜豆素 C：一种来自新型海绵的具有细胞毒性的大环内酯及其开环衍生物。
J Nat Prod. 2022 Apr 22;85(4):1059-1066. doi: 10.1021/acs.jnatprod.1c01179. Epub 2022 Mar 2.
2
Tetrahydropyranyl: A Non-aromatic, Mild-Acid-Labile Group for Hydroxyl Protection in Solid-Phase Peptide Synthesis.四氢吡喃基：用于固相肽合成中羟基保护的非芳香性、对弱酸不稳定的基团。
ChemistryOpen. 2017 Mar 8;6(2):206-210. doi: 10.1002/open.201600157. eCollection 2017 Apr.
3
Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry.理解四氢吡喃基作为肽化学中的保护基团
ChemistryOpen. 2017 Mar 8;6(2):168-177. doi: 10.1002/open.201600156. eCollection 2017 Apr.
4
Synthesis of complex head-to-side-chain cyclodepsipeptides.复杂的头至侧链环缩肽的合成
Nat Protoc. 2016 Oct;11(10):1924-1947. doi: 10.1038/nprot.2016.116. Epub 2016 Sep 15.
5
Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds.非蛋白氨基酸砌块用于构建非核糖体肽和杂合聚酮骨架。
Angew Chem Int Ed Engl. 2013 Jul 8;52(28):7098-124. doi: 10.1002/anie.201208344. Epub 2013 May 31.
6
"Head-to-side-chain" cyclodepsipeptides of marine origin.海洋来源的“头到侧链”环二肽。
Mar Drugs. 2013 May 21;11(5):1693-717. doi: 10.3390/md11051693.
7
Cyclodepsipeptides from marine sponges: natural agents for drug research.海洋海绵中环肽：药物研究的天然试剂。
Mar Drugs. 2010 Mar 22;8(3):810-34. doi: 10.3390/md8030810.
8
Synthesis and cytotoxicity of desmethoxycallipeltin B: lack of a quinone methide for the cytotoxicity of callipeltin B.去甲氧基愈创木素B的合成与细胞毒性：愈创木素B细胞毒性中醌甲基化物的缺失
Bioorg Med Chem Lett. 2007 Sep 15;17(18):5136-8. doi: 10.1016/j.bmcl.2007.07.003. Epub 2007 Jul 7.
本文引用的文献
1
Solid-phase synthesis and configurational reassigment of callipeltin E. Implications for the structures of callipeltins A and B.Callipeltin E的固相合成与构型重新确定。对Callipeltins A和B结构的启示。
J Org Chem. 2006 Aug 18;71(17):6351-6. doi: 10.1021/jo060351h.
2
Complete stereochemistry of neamphamide A and absolute configuration of the beta-methoxytyrosine residue in papuamide B.新海鞘酰胺A的完整立体化学及巴布亚酰胺B中β-甲氧基酪氨酸残基的绝对构型。
J Org Chem. 2005 Aug 19;70(17):6842-7. doi: 10.1021/jo0508853.
3
Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A.β-甲氧基酪氨酸所有立体异构体的简洁合成及Callipeltin A中残基绝对构型的测定。
Org Lett. 2005 Aug 4;7(16):3585-8. doi: 10.1021/ol0513600.
4
Stereoselective synthesis of four stereoisomers of beta-methoxytyrosine, a component of callipeltin A.β-甲氧基酪氨酸四种立体异构体的立体选择性合成，callipeltin A的一个组分。
J Org Chem. 2005 Apr 15;70(8):3120-6. doi: 10.1021/jo047876z.
5
Diastereoselective synthesis of all stereoisomers of beta-methoxytyrosine, a component of papuamides.巴布亚酰胺的一种成分β-甲氧基酪氨酸所有立体异构体的非对映选择性合成。
J Org Chem. 2002 Dec 27;67(26):9210-5. doi: 10.1021/jo0258352.
Zotero 插件