甘露肽霉素 - E糖基化酪氨酸部分的氮杂类似物的合成。
Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.
作者信息
Guppi Sanjeeva R, O'Doherty George A
机构信息
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
出版信息
J Org Chem. 2007 Jun 22;72(13):4966-9. doi: 10.1021/jo070326r. Epub 2007 May 26.
Abstract
Two C4' amido disaccharide analogues of mannopeptimycin-E were synthesized via an iterative palladium glycosylation sequence. The stereoselective synthesis of the C4' acylated 1,4-alpha,alpha-manno,manno-amido disaccharide has been achieved in ten steps from a protected d-tyrosine. The path relies upon a regio- and diastereoselective palladium-catalyzed azide substitution reaction. The competence of the synthesis is demonstrated by the good overall yield (21%) from protected tyrosine.
摘要
通过迭代钯糖基化序列合成了甘露肽霉素-E的两种C4'酰胺基二糖类似物。从受保护的d-酪氨酸出发，经过十步反应实现了C4'酰化的1,4-α,α-甘露糖基、甘露糖基酰胺基二糖的立体选择性合成。该合成路径依赖于区域和非对映选择性钯催化的叠氮化物取代反应。从受保护的酪氨酸出发获得的良好总产率（21%）证明了该合成方法的有效性。
相似文献
1
Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.甘露肽霉素 - E糖基化酪氨酸部分的氮杂类似物的合成。
J Org Chem. 2007 Jun 22;72(13):4966-9. doi: 10.1021/jo070326r. Epub 2007 May 26.
2
Synthetic studies toward mannopeptimycin-E: synthesis of the O-linked tyrosine 1,4-alpha,alpha-manno,manno-pyranosyl pyranoside.对甘露肽霉素 - E的合成研究：O - 连接酪氨酸1,4 - α,α - 甘露糖基、甘露糖基吡喃糖苷的合成
Org Lett. 2006 Apr 13;8(8):1605-8. doi: 10.1021/ol060254a.
3
Titanocene(III) chloride mediated radical induced allylation of aldimines: formal synthesis of C-linked 4'-deoxy aza-disaccharide.三氯化钛介导的自由基诱导的亚胺烯丙基化反应：C 连接的 4'-去氧氮杂二糖的形式合成。
J Org Chem. 2011 Sep 2;76(17):7229-34. doi: 10.1021/jo200908b. Epub 2011 Aug 5.
4
A general, two-directional approach to aza-C-(1 --> 1)-linked disaccharide mimetics.
Chem Commun (Camb). 2005 Mar 28(12):1646-8. doi: 10.1039/b417899h. Epub 2005 Feb 2.
5
A convenient synthesis of novel aza-C-disaccharide analogues.新型氮杂-C-二糖类似物的简便合成方法。
Carbohydr Res. 2014 Oct 29;398:36-9. doi: 10.1016/j.carres.2014.05.016. Epub 2014 Jun 4.
6
The parallel synthesis of a disaccharide library using a solid phase, peptide-templated strategy.采用固相肽模板策略对二糖文库进行平行合成。
Chem Commun (Camb). 2004 Feb 21(4):454-5. doi: 10.1039/b313571c. Epub 2003 Dec 12.
7
Solid-phase synthesis of an O-linked glycopeptide based on a benzyl-protected glycan approach.
Carbohydr Res. 1996 Oct 4;292:71-81. doi: 10.1016/s0008-6215(96)91027-7.
8
Stereoselective synthesis of the disaccharide unit of incednine.靛因二糖单位的立体选择性合成。
Org Lett. 2013 Jan 4;15(1):62-4. doi: 10.1021/ol303093z. Epub 2012 Dec 18.
9
Unlocking ylide reactivity in the metal-catalyzed allylic substitution reaction: stereospecific construction of primary allylic amines with aza-ylides.解锁金属催化烯丙基取代反应中的叶立德反应活性：用氮杂叶立德立体专一性构建伯烯丙基胺
J Am Chem Soc. 2009 Jul 1;131(25):8722-3. doi: 10.1021/ja9041302.
10
Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.通过 N-磷酰基-N-烯丙基-炔酰胺的氮杂-Claisen 重排实现烯丙基烯酮亚胺的碳环化级联反应。
Org Lett. 2012 Apr 6;14(7):1768-71. doi: 10.1021/ol300366e. Epub 2012 Mar 13.
引用本文的文献
1
Comprehensive review of chemical strategies for the preparation of new aminoglycosides and their biological activities.新氨基糖苷类化合物的化学合成策略及其生物活性的综合评述。
Chem Soc Rev. 2018 Feb 19;47(4):1189-1249. doi: 10.1039/c7cs00407a.
2
Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine.通过Sonogashira反应实现保护型酪氨酸的功能化：3-(1,2,3-三唑基)-酪氨酸的合成
Mol Divers. 2016 May;20(2):469-81. doi: 10.1007/s11030-015-9642-y. Epub 2015 Oct 26.
3
A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides.2,3-二脱氧己-2-烯吡喃糖苷近期合成应用综述。
Molecules. 2015 May 8;20(5):8357-94. doi: 10.3390/molecules20058357.
4
De novo synthesis and biological evaluation of C6″-substituted C4″-amide analogues of SL0101.SL0101的C6″-取代C4″-酰胺类似物的从头合成及生物学评价
Org Lett. 2014 Nov 21;16(22):5996-9. doi: 10.1021/ol503012k. Epub 2014 Nov 5.
5
Merremoside D: de novo synthesis of the purported structure, NMR analysis, and comparison of spectral data.莫雷罗苷 D：推测结构的从头合成、NMR 分析和光谱数据比较。
Org Lett. 2014 Jan 17;16(2):492-5. doi: 10.1021/ol403369h. Epub 2013 Dec 19.
6
Structural and functional characterization of MppR, an enduracididine biosynthetic enzyme from streptomyces hygroscopicus: functional diversity in the acetoacetate decarboxylase-like superfamily.耐酸菌 MppR 的结构与功能分析：来自吸水链霉菌的持久霉素生物合成酶；乙酰乙酸脱羧酶超家族的功能多样性。
Biochemistry. 2013 Jul 2;52(26):4492-506. doi: 10.1021/bi400397k. Epub 2013 Jun 21.
7
De Novo Asymmetric Syntheses of d-, l- and 8-epi-Swainsonine.d-、l-和8-表-斯氏紫堇碱的从头不对称合成
Tetrahedron. 2008 Jan 7;64(2):304-313. doi: 10.1016/j.tet.2007.10.109.
本文引用的文献
1
De novo asymmetric synthesis of D- and L-swainsonine.D-和L-苦马豆素的从头不对称合成
Org Lett. 2006 Apr 13;8(8):1609-12. doi: 10.1021/ol0602811.
2
Synthetic studies toward mannopeptimycin-E: synthesis of the O-linked tyrosine 1,4-alpha,alpha-manno,manno-pyranosyl pyranoside.对甘露肽霉素 - E的合成研究：O - 连接酪氨酸1,4 - α,α - 甘露糖基、甘露糖基吡喃糖苷的合成
Org Lett. 2006 Apr 13;8(8):1605-8. doi: 10.1021/ol060254a.
3
De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.通过钯催化的N-糖基化反应从头不对称合成同型腺苷。
Org Lett. 2006 Jan 19;8(2):293-6. doi: 10.1021/ol052664p.
4
Hydrophobic acetal and ketal derivatives of mannopeptimycin-alpha and desmethylhexahydromannopeptimycin-alpha: semisynthetic glycopeptides with potent activity against Gram-positive bacteria.甘露肽霉素-α和去甲基六氢甘露肽霉素-α的疏水缩醛和缩酮衍生物：对革兰氏阳性菌具有强效活性的半合成糖肽。
J Med Chem. 2004 Jul 1;47(14):3487-90. doi: 10.1021/jm049765y.
5
De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction.使用钯催化糖基化反应进行寡糖的从头合成。
J Am Chem Soc. 2004 Mar 24;126(11):3428-9. doi: 10.1021/ja039400n.
6
Comparative in vitro activities of AC98-6446, a novel semisynthetic glycopeptide derivative of the natural product mannopeptimycin alpha, and other antimicrobial agents against gram-positive clinical isolates.新型半合成糖肽衍生物AC98 - 6446（天然产物甘露肽霉素α的衍生物）与其他抗菌药物对革兰氏阳性临床分离株的体外比较活性。
Antimicrob Agents Chemother. 2004 Mar;48(3):739-46. doi: 10.1128/AAC.48.3.739-746.2004.
7
Mannopeptimycin esters and carbonates, potent antibiotic agents against drug-resistant bacteria.甘露肽霉素酯和碳酸酯，对抗耐药菌的强效抗生素。
Bioorg Med Chem Lett. 2004 Jan 5;14(1):279-82. doi: 10.1016/j.bmcl.2003.09.071.
8
Synthesis of the apratoxin 2,4-disubstituted thiazoline via an intramolecular aza-Wittig reaction.通过分子内氮杂维蒂希反应合成阿普拉毒素2,4-二取代噻唑啉。
Org Lett. 2003 Apr 17;5(8):1281-3. doi: 10.1021/ol0342148.
9
Novel ether derivatives of mannopeptimycin glycopeptide antibiotic.甘露糖肽霉素糖肽抗生素的新型醚衍生物
Bioorg Med Chem Lett. 2003 Mar 24;13(6):1151-5. doi: 10.1016/s0960-894x(03)00045-3.
10
Mannopeptimycins, new cyclic glycopeptide antibiotics produced by Streptomyces hygroscopicus LL-AC98: antibacterial and mechanistic activities.甘露肽霉素，由吸水链霉菌LL-AC98产生的新型环状糖肽抗生素：抗菌活性及作用机制
Antimicrob Agents Chemother. 2003 Jan;47(1):62-9. doi: 10.1128/AAC.47.1.62-69.2003.
Zotero 插件