The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

LU Dongtao; LIU Chao; QIN Luping; ZOU Yan

doi:10.3969/j.issn.1006-0111.2019.05.011

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Volume 37 Issue 5

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2019 > 37(5): 444-449

LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011

Citation:

LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011

The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

doi: 10.3969/j.issn.1006-0111.2019.05.011

1.
Department of Pharmacy, Changhai Hospital, Naval Medical University, Shanghai 200433, China
2.
School of Pharmacy, Naval Medical University, Shanghai 200433, China

Received Date: 2018-10-31
Rev Recd Date: 2019-02-13

Abstract

Objective The marine cyclopeptide stylissamide Ⅰ was synthesized through a solid phase synthesis and cyclization in solution(SPS-CS). Methods 2-chlorotrityl chloride resin was used as solid support for the total synthesis.Each amino acid protected by 9-fluorenylmethyloxycarbonyl(Fmoc) group was coupled with N,N-diisopropylethylamine(DIPEA)/O-(6-chloro-1-hydrocibenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro- phosphat(HCTU) as condensing agents.The linear peptide was cleaved from resin by 2,2,2-trifluoroethanol(TFE) and cyclized in the presence of(7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate(PyAOP)/1-hydroxy-7-azabenzotriazole(HOAt)/N-methyl morphofine(NMM).Finally,the crude cyclopeptide was obtained through global deprotection with trifluoroacetic acid(TFA).The target compound was purified by preparative RP-HPLC to 98.9% pure and its structure was identified by ¹H-NMR,¹³C-NMR and Q-TOF LC/MS. Results The first total synthesis of the marine cyclopeptide stylissamide Ⅰ was successfully realized with a yield of 67%. Conclusion A rapid,simple and high-efficient method of stylissamide Ⅰ total synthesis was successfully established.
- stylissamide Ⅰ,
- solid phase synthesis,
- cyclopeptide

References

[1]	NORO J C,KALAITZIS J A,NEILAN B A.Bioactive natural products from Papua New Guinea marine sponges[J].Chem Biodivers,2012,9(10):2077-2095.
[2]	PROKSCH P,EBEL R,EDRADA R A,et al.Bioactive natural products from marine invertebrates and associated fungi[J].Prog Mol Subcell Biol,2003,37:117-142.
[3]	ANDAVAN G S,LEMMENS-GRUBER R.Cyclodepsipeptides from marine sponges:Natural agents for drug research[J].Mar Drugs,2010,8(3):810-834.
[4]	PIFFERI C,BERTHET N,RENAUDET O.Cyclopeptide scaffolds in carbohydrate-based synthetic vaccines[J].Biomater Sci,2017,5(5):953-965.
[5]	KURANAGA T,SESOKO Y,INOUE M.Cu-mediated enamide formation in the total synthesis of complex peptide natural products[J].Nat Prod Rep,2014,31(4):514-532.
[6]	RUSSO A,AIELLO C,GRIECO P,et al.Targeting "undruggable" proteins:design of synthetic cyclopeptides[J].Curr Med Chem,2016,23(8):748-762.
[7]	DAHIYA R,GAUTAM H.Toward the synthesis and biological screening of a cyclotetrapeptide from marine bacteria[J].Mar Drugs,2010,9(1):71-81.
[8]	CHANDRA K,ROY T K,SHALEV D E,et al.A tandem in situ peptide cyclization through trifluoroacetic acid cleavage[J].Angew Chem Int Ed Engl,2014,53(36):9450-9455.
[9]	DALETOS G,KALSCHEUER R,KOLIWER-BRANDL H,et al.Callyaerins from the marine sponge Callyspongia aerizusa:Cyclic peptides with antitubercular activity[J].J Nat Prod,2015,78(8):1910-1925.
[10]	ZHOU X,HUANG H,CHEN Y,et al.Marthiapeptide A,an anti-infective and cytotoxic polythiazole cyclopeptide from a 60 L scale fermentation of the deep sea-derived Marinactinospora thermotolerans SCSIO 00652[J].J Nat Prod,2012,75(12):2251-2255.
[11]	KANG K B,MING G,KIM G J,et al.Jubanines F-J,cyclopeptide alkaloids from the roots of Ziziphus jujuba[J].Phytochemistry,2015,119:90-95.
[12]	ESMAEILI M A,ABAGHERI-MAHABADI N,HASHEMPOUR H,et al.Viola plant cyclotide vigno 5 induces mitochondria-mediated apoptosis via cytochrome C release and caspases activation in cervical cancer cells[J].Fitoterapia,2016,109:162-168.
[13]	THEVENARD J,RAMONT L,DEVY J,et al.The YSNSG cyclopeptide derived from tumstatin inhibits tumor angiogenesis by down-regulating endothelial cell migration[J].Int J Cancer,2010,126(5):1055-1066.
[14]	FESTA C,DE MARINO S,SEPE V,et al.Solomonamides A and B,new anti-inflammatory peptides from Theonella swinhoei[J].Org Lett,2011,13(6):1532-1535.
[15]	SONG L,WANG Z,WANG Y,et al.Natural Cyclopeptide RA-XⅡ,a new autophagy inhibitor,suppresses protective autophagy for enhancing apoptosis through AMPK/mTOR/P70S6K pathways in HepG2 cells[J].Molecules,2017,22(11):1934.
[16]	SCHMIDT G,GRUBE A,KÖCK M.Stylissamides A-D new proline-containing cyclic heptapeptides from the marine sponge Stylissa caribica[J].Eur J Org Chem,2007,2007(24):4103-4110.
[17]	CYCHON C,KÖCK M.Stylissamides E and F,cyclic heptapeptides from the caribbean sponge Stylissa caribica[J].J Nat Prod,2010,73(4):738-742.
[18]	CYCHON C,SCHMIDT G,KÖCK M.Sequencing of cyclic peptides by NMR and MS techniques demonstrated on stylissamides A-F[J].Phytochem Rev,2013,12(3):495-505.
[19]	KUBOTA T,KOBAYASHI J,NAKAMURA K,et al.stylissamide Ⅰ,a new cyclic heptapeptide from an okinawan marine sponge Stylissa sp.[J].Heterocycles,2017,95(2):799-806.
[20]	刘雷明,王国亮,王建华,等.AoGDW肽固相合成工艺研究[J].化学试剂,2009,31(11):871-874.
[21]	RIJKERS D T S,KRUIJTZER J A W,KILLIAN J A,et al.A convenient solid phase synthesis of S-palmitoyl transmembrane peptides[J].Tetrahedron Lett,2005,46(19):3341-3345.
[22]	CHEN Y,LIU C,LIU N,et al.Total synthesis and antibacterial study of cyclohexapeptides desotamide B,wollamide B and their analogs[J].Chem Biodivers,2017,15(1):e1700414.
[23]	LIU C,ZOU Y,SONG H,et al.Arylboronate ester protected amino acids as orthogonal building blocks for fmoc solid phase peptide synthesis[J].Eur J Org Chem,2017,2017(39):5916-5920.
[24]	HUMPHREY J M,CHAMBERLIN A R.Chemical synthesis of natural product peptides:coupling methods for the incorporation of non-coded amino acids into peptides[J].Chem Rev,1997,97(6):2243-2266.
[25]	LIU C,CHEN X,ZHI X,et al.Structure-based development of an osteoprotegerin-like glycopeptide that blocks RANKL/RANK interactions and reduces ovariectomy-induced bone loss in mice[J].Eur J Med Chem,2018,145:661-672.
[26]	HU H,XUE J,SWARTS B M,et al.Synthesis and antibacterial activities of N-glycosylated derivatives of tyrocidine A,a macrocyclic peptide antibiotic[J].J Med Chem,2009,52(7):2052-2059.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

1. Department of Pharmacy, Changhai Hospital, Naval Medical University, Shanghai 200433, China

2. School of Pharmacy, Naval Medical University, Shanghai 200433, China

Received Date: 2018-10-31

Rev Recd Date: 2019-02-13

Key words:

Abstract: Objective The marine cyclopeptide stylissamide Ⅰ was synthesized through a solid phase synthesis and cyclization in solution(SPS-CS). Methods 2-chlorotrityl chloride resin was used as solid support for the total synthesis.Each amino acid protected by 9-fluorenylmethyloxycarbonyl(Fmoc) group was coupled with N,N-diisopropylethylamine(DIPEA)/O-(6-chloro-1-hydrocibenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro- phosphat(HCTU) as condensing agents.The linear peptide was cleaved from resin by 2,2,2-trifluoroethanol(TFE) and cyclized in the presence of(7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate(PyAOP)/1-hydroxy-7-azabenzotriazole(HOAt)/N-methyl morphofine(NMM).Finally,the crude cyclopeptide was obtained through global deprotection with trifluoroacetic acid(TFA).The target compound was purified by preparative RP-HPLC to 98.9% pure and its structure was identified by ¹H-NMR,¹³C-NMR and Q-TOF LC/MS. Results The first total synthesis of the marine cyclopeptide stylissamide Ⅰ was successfully realized with a yield of 67%. Conclusion A rapid,simple and high-efficient method of stylissamide Ⅰ total synthesis was successfully established.

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[1]	NORO J C,KALAITZIS J A,NEILAN B A.Bioactive natural products from Papua New Guinea marine sponges[J].Chem Biodivers,2012,9(10):2077-2095.
[2]	PROKSCH P,EBEL R,EDRADA R A,et al.Bioactive natural products from marine invertebrates and associated fungi[J].Prog Mol Subcell Biol,2003,37:117-142.
[3]	ANDAVAN G S,LEMMENS-GRUBER R.Cyclodepsipeptides from marine sponges:Natural agents for drug research[J].Mar Drugs,2010,8(3):810-834.
[4]	PIFFERI C,BERTHET N,RENAUDET O.Cyclopeptide scaffolds in carbohydrate-based synthetic vaccines[J].Biomater Sci,2017,5(5):953-965.
[5]	KURANAGA T,SESOKO Y,INOUE M.Cu-mediated enamide formation in the total synthesis of complex peptide natural products[J].Nat Prod Rep,2014,31(4):514-532.
[6]	RUSSO A,AIELLO C,GRIECO P,et al.Targeting "undruggable" proteins:design of synthetic cyclopeptides[J].Curr Med Chem,2016,23(8):748-762.
[7]	DAHIYA R,GAUTAM H.Toward the synthesis and biological screening of a cyclotetrapeptide from marine bacteria[J].Mar Drugs,2010,9(1):71-81.
[8]	CHANDRA K,ROY T K,SHALEV D E,et al.A tandem in situ peptide cyclization through trifluoroacetic acid cleavage[J].Angew Chem Int Ed Engl,2014,53(36):9450-9455.
[9]	DALETOS G,KALSCHEUER R,KOLIWER-BRANDL H,et al.Callyaerins from the marine sponge Callyspongia aerizusa:Cyclic peptides with antitubercular activity[J].J Nat Prod,2015,78(8):1910-1925.
[10]	ZHOU X,HUANG H,CHEN Y,et al.Marthiapeptide A,an anti-infective and cytotoxic polythiazole cyclopeptide from a 60 L scale fermentation of the deep sea-derived Marinactinospora thermotolerans SCSIO 00652[J].J Nat Prod,2012,75(12):2251-2255.
[11]	KANG K B,MING G,KIM G J,et al.Jubanines F-J,cyclopeptide alkaloids from the roots of Ziziphus jujuba[J].Phytochemistry,2015,119:90-95.
[12]	ESMAEILI M A,ABAGHERI-MAHABADI N,HASHEMPOUR H,et al.Viola plant cyclotide vigno 5 induces mitochondria-mediated apoptosis via cytochrome C release and caspases activation in cervical cancer cells[J].Fitoterapia,2016,109:162-168.
[13]	THEVENARD J,RAMONT L,DEVY J,et al.The YSNSG cyclopeptide derived from tumstatin inhibits tumor angiogenesis by down-regulating endothelial cell migration[J].Int J Cancer,2010,126(5):1055-1066.
[14]	FESTA C,DE MARINO S,SEPE V,et al.Solomonamides A and B,new anti-inflammatory peptides from Theonella swinhoei[J].Org Lett,2011,13(6):1532-1535.
[15]	SONG L,WANG Z,WANG Y,et al.Natural Cyclopeptide RA-XⅡ,a new autophagy inhibitor,suppresses protective autophagy for enhancing apoptosis through AMPK/mTOR/P70S6K pathways in HepG2 cells[J].Molecules,2017,22(11):1934.
[16]	SCHMIDT G,GRUBE A,KÖCK M.Stylissamides A-D new proline-containing cyclic heptapeptides from the marine sponge Stylissa caribica[J].Eur J Org Chem,2007,2007(24):4103-4110.
[17]	CYCHON C,KÖCK M.Stylissamides E and F,cyclic heptapeptides from the caribbean sponge Stylissa caribica[J].J Nat Prod,2010,73(4):738-742.
[18]	CYCHON C,SCHMIDT G,KÖCK M.Sequencing of cyclic peptides by NMR and MS techniques demonstrated on stylissamides A-F[J].Phytochem Rev,2013,12(3):495-505.
[19]	KUBOTA T,KOBAYASHI J,NAKAMURA K,et al.stylissamide Ⅰ,a new cyclic heptapeptide from an okinawan marine sponge Stylissa sp.[J].Heterocycles,2017,95(2):799-806.
[20]	刘雷明,王国亮,王建华,等.AoGDW肽固相合成工艺研究[J].化学试剂,2009,31(11):871-874.
[21]	RIJKERS D T S,KRUIJTZER J A W,KILLIAN J A,et al.A convenient solid phase synthesis of S-palmitoyl transmembrane peptides[J].Tetrahedron Lett,2005,46(19):3341-3345.
[22]	CHEN Y,LIU C,LIU N,et al.Total synthesis and antibacterial study of cyclohexapeptides desotamide B,wollamide B and their analogs[J].Chem Biodivers,2017,15(1):e1700414.
[23]	LIU C,ZOU Y,SONG H,et al.Arylboronate ester protected amino acids as orthogonal building blocks for fmoc solid phase peptide synthesis[J].Eur J Org Chem,2017,2017(39):5916-5920.
[24]	HUMPHREY J M,CHAMBERLIN A R.Chemical synthesis of natural product peptides:coupling methods for the incorporation of non-coded amino acids into peptides[J].Chem Rev,1997,97(6):2243-2266.
[25]	LIU C,CHEN X,ZHI X,et al.Structure-based development of an osteoprotegerin-like glycopeptide that blocks RANKL/RANK interactions and reduces ovariectomy-induced bone loss in mice[J].Eur J Med Chem,2018,145:661-672.
[26]	HU H,XUE J,SWARTS B M,et al.Synthesis and antibacterial activities of N-glycosylated derivatives of tyrocidine A,a macrocyclic peptide antibiotic[J].J Med Chem,2009,52(7):2052-2059.

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The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

doi: 10.3969/j.issn.1006-0111.2019.05.011

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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