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FU Donglin, RAO Xuemin, XU Jinyi, XIE Weijia, WU Xiaoming. Total synthesis of cyclodepsipeptide Hikiamides A-C[J]. Journal of China Pharmaceutical University, 2018, 49(2): 181-186. DOI: 10.11665/j.issn.1000-5048.20180207
Citation: FU Donglin, RAO Xuemin, XU Jinyi, XIE Weijia, WU Xiaoming. Total synthesis of cyclodepsipeptide Hikiamides A-C[J]. Journal of China Pharmaceutical University, 2018, 49(2): 181-186. DOI: 10.11665/j.issn.1000-5048.20180207

Total synthesis of cyclodepsipeptide Hikiamides A-C

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  • Total synthesis of cyclodepsipeptide Hikiamides A - C was described. Fragment convergent condensation method was applied for the preparation of Hikiamides A - C , starting from Commercially available amino acid such as L-N-Boc-Phe-OH, L-N-Boc-Trp-OH, L-N-Cbz-Van-OH etc. Tripeptide fragments(compounds 5a / 5b )and dipeptide fragments(compounds 8a / 8b )were first prepared. The subsequent condensation of the resulted two fragments provided protected linear pentapetides(compounds 9a / 9b / 9c ); Finally, the linear pentapetide was cyclized by a mixed condensing agents comprised of PyBOP and HBTU. Hikiamides A - C was obtained with total yields of 9%, 11% and 6. 5%, respectively. Compared with the natural source, this method has the advantages of low cost, convenient operation and high yield, which effectively solves the problem of low isolated yield of Hikiamides A - C from Fusarium sp.
  • [1]
    Wang T,Yin XX.Advances in therapeutics of type 2 diabetes mellitus[J].Prog Pharm Sci(药学进展),2016,40(5):323-330.
    [2]
    Zhao Y,Lin W,Li Z,et al.High expression of mannose-binding lectin and the risk of vascular complications of diabetes:evidence from a meta-analysis[J].Diabetes Technol Ther,2015,17(7):490-497.
    [3]
    Zhu XW,Deng FY,Wu LF,et al.Functional mechanisms for type 2 diabetes-associated genetic variants[J].J Diabetes Complicat,2015,29(4):497-501.
    [4]
    Seuring T,Archangelidi O,Suhrcke M.The economic costs of type 2 diabetes:a global systematic review[J].Pharmaco Economics,2015,33(8):811-831.
    [5]
    Poomalar GK.Changing trends in management of gestational diabetes mellitus[J].World J Diabetes,2015,6(2):284-295.
    [6]
    Gross B,Staels B.PPAR agonists:multimodal drugs for the treatment of type-2 diabetes[J].Best Pract Res Clin Endocrinol Metab,2007,21(4):687-710.
    [7]
    Schernthaner G,Currie CJ,Schernthaner GH.Do we still need pioglitazone for the treatment of type 2 diabetes? A risk-benefit critique in 2013[J].Dibetes Care,2013,36(2):155-160.
    [8]
    Fukuda T,Sudoh Y,Tsuchiya Y,et al.Hikiamides A-C,cyclic pentadepsipeptides from fusarium sp.tama 456[J].J Nat Prod,2015,78(4):797-802.
    [9]
    Gleeson EC,Jackson WR,Robinson AJ.Ring-closing metathesis in peptides[J].Tetrahedron Lett,2016,57(39):4325-4333.
    [10]
    Pan ZY,Wu CL,Wang W,et al.Total synthesis and stereochemical assignment of gymnopeptides A and B[J].Org Lett,2017,19(17):4420-4423.
    [11]
    Zhang S,Amso Z,Kaur H,et al.Synthesis of natural cyclopentapeptides isolated from dianthus chinensis[J].J Nat Prod,2016,79(7):1769-1774.
    [12]
    Scherkenbeck J,Lüttenberg S,Ludwig M,et al.Segment solid-phase total synthesis of the anthelmintic cyclooctadepsipeptides PF1022A and emodepside[J].Eur J Org Chem,2012,2012(8):1546-1553.
    [13]
    Maharani R,Brownlee RTC,Hughes AB,et al.A total synthesis of a highly N-methylated cyclodepsipeptide [2s,3s-Hmp]-aureobasidin l using solid-phase methods[J].Tetrahedron,2014,70(14):2351-2358.
    [14]
    He W,Qiu HB,Chen YJ,et al.Total synthesis of proposed structure of coibamide a,a highly N- and O-methylated cytotoxic marine cyclodepsipeptide[J].Tetrahedron Lett,2014,55(44):6109-6112.
    [15]
    Elagawany M,Ibrahim MA.An improved route for the synthesis of rolloamide B[J].Tetrahedron Lett,2016,57(34):3837-3840.
    [16]
    Carroll CL,Johnston JV,Kekec A,et al.Synthesis and cytotoxicity of novel sansalvamide A derivatives[J].Org Lett,2005,7(16):3481-3484.
    [17]
    Rodriguez RA,Pan PS,Pan CM,et al.Synthesis of second-generation sansalvamide A derivatives:novel templates as potential antitumor agents[J].J Org Chem,2007,72(6):1981-1987.

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