Journal of Guangxi Normal University(Natural Science Edition) ›› 2011, Vol. 29 ›› Issue (2): 56-60.

Previous Articles     Next Articles

Synthesis and Crystal Structure of Conformationally Constrained Peptides with a Trans-2,3-diaryl-1-aminocyclopropanecarboxylic Acid Residue

HUANG Wan-yun1, SU Gui-fa1, PAN Cheng-xue1, QIN Jiang-ke1, TANG Huang1, YI Xiang-hui2   

  1. 1.State Key Laboratory Cultivation Base for the Chemistry andMolecular Engineering of Medicinal Resources, College of Chemistry and Chemical Engineering,Guangxi Normal University,Guilin Guangxi 541004,China;
    2.Department of Chemistry and Chemical Engineering,Guilin Normal College,Guilin Guangxi 541001,China
  • Received:2011-03-21 Published:2018-11-19

Abstract: Two diastereomers of conformationally constrained dipeptides with a trans-2,3-diaryl-1-aminocyclopropanecarboxylic acid residue were synthesized from L-Phenylalanine methyl ester and racemic 1-(4-Methoxy-phenyl)-2,5-diphenyl-6-oxa-4-aza-spiro[2.4]hept-4-en-7-one utilized the oxazolone method,and the structures of them were studied by means of X-ray single crystal diffraction analysis.

Key words: conformationally constrained peptide, oxazolone method, synthesis, crystal structure

CLC Number: 

  • O629.72
[1] GRAUER A,KOENIG B.Peptidomimetics-A versatile route to biologically active compounds[J].Eur JOrg Chem,2009,30:5099-5111.
[2] WU Yun-dong,GELLMAN S.Peptidomimetics[J].Acc Chem Res,2008,41(10):1231-1232.
[3] VASS E,HOLLOSI M,BESSON F,et al.Vibrational spectroscopic detection of β-and γ-turns in synthetic and natural peptides and proteins[J].Chem Rev,2003,103:1917-1954.
[4] HANESSIAN S,MAJI D K,GOVINDAN S,et al.Substrate controlled and organocatalytic asymmetric synthesis of carbocyclic amino acid dipeptide mimetics[J].J Org Chem,2010,75(9):2861-2876.
[5] GRAUER A A,CABRELE C,ZABEL M,et al.Stable right-and left-handedpeptide helices containing Cα-tetrasubstituted α-amino acids[J].J Org Chem,2009,74(10):3718-3726.
[6] JIME′NEZ A I,BALLANO G,CATIVIELA C.First observation of two consecutive γ-turns in a crystalline linear dipeptide[J].Angew Chem Int Ed,2005,44:396-399.
[7] ROYO S,BORGGRAEVE W M D,PEGGION C,et al.Turn and helical peptide handedness governed exclusively by side-chain chiral centers[J].J Am Chem Soc,2005,127:2036-2037.
[8] JIMENEZ A I,CATIVIELA C,GOMEZ-CATALAN,et al.Influence of side chain restriction and NH…π interaction on the β-turn folding modes of dipeptides incorporating phenylalanine cyclohexane derivatives[J].J Am Chem Soc,2000,122:5811-5821.
[9] SU Gui-fa,MU Hong-tao,ZA Dan-ming,et al.Stereospecific synthesis of trans-2,3-diaryl substituted 1-aminocyclopropanecarboxylic acid derivatives[J].Synth Commun,2003,33(16):2873-2884.
[10] 苏桂发,潘成学,曾陇梅,等.反式2,3-二芳基取代-1-氨基环丙烷羧酸的合成及其结构研究[J].化学学报,2004,62(19):1941-1947.
[11] PAN Cheng-xue,SU Gui-fa,QIN Jiang-ke.Diastereospecific synthesis of trans-2,3-diaryl-substituted 1-aminocyclopropanecarboxylic acids[J].Org Prep Proced Int,2005,37(3):239-246.
[12] 潘成学,苏桂发.非对映立体专一性合成二芳基取代环丙烷氨基酸及晶体结构[J].广西师范大学学报:自然科学版,2006,24(3):64-67.
[13] SHELDRICK G M.SHELXS-97,program for the solution of crystal structures[CP/CD].Go¨ttingen,Germany:University of Go¨ttingen,1997.
[14] SHELDRICK G M.SHELXL-97,program for the refinement of crystal structures[CP/CD].Go¨ttingen,Germany:Universityof Go¨ttingen,1997.
[1] XIE Tingting, XIE Yao, NI Qingling. Synthesis, Characterization and Crystal Structures of Complexes ContainingOrganic Phosphine Gold Acetylene and Triazoles [J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(4): 92-99.
[2] XU Peng, LI Chaofeng, CHANG Xinwei, ZHANG Yanwu. Synthesis of Water-Soluble Ketone-Aldehyde Resins by Catalysis of Solid Base [J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(3): 70-79.
[3] HUANG Xueren, ZHAO Zhiyuan, JIANG Yimin. Synthesis, Crystal Structure and Luminescent Properties ofa New 2D Coordination Polymer of Zn(Ⅱ)-ttp(4′-(4-carboxyphenyl) -2,2′:6′,2″-terpyridine) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2016, 34(2): 98-104.
[4] WANG Yana, LIN Jiahuang, NI Qingling, ZHANG Fang, YU Ronghua, WANG Xiujian. Synthesis and Crystal Structure of 2-[1,3-bis(2-hydroxy benzyl)-5-pyridyl-4-imidazolidinyl] phenol [J]. Journal of Guangxi Normal University(Natural Science Edition), 2016, 34(2): 105-110.
[5] LIU Han-fu, MA Xian-li, CHEN Su-yi , SHEN Xue-song, HUANG Fu-ping. Synthesis and Antibacterial Activity of Ternary Zinc Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(4): 103-107.
[6] LIANG Xiao-long, HUANG Wan-yun, PAN Cheng-xue, SU Gui-fa. Synthesis and Crystal Structure of Ethyl 5-acetamido-4-(4-chlorophenyl)-2-methyl-6-oxo-5, 6-dihydro-4H-pyran-3-carboxylate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(2): 82-87.
[7] JIANG Li-ping, HUANG Wan-yun, LIU Dong-cheng, LIANG Fu-pei. Synthesis and Crystal Structures of Zn(Ⅱ) and Cu(Ⅱ) Complexes of 2,2′-dihydroxy[1,1′-binaphthalene]-3,3′-dicarbonylbis(salicylaldehydehydrazone) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(1): 93-98.
[8] HUO Hong-yue, LI Zhong-qing, QIN Qi-pin, LIU Yan-cheng, CHEN Zhen-feng. Crystal Structure and Antitumor Activity of Zinc(Ⅱ) Complex with Schiff Bases Derived from 2-Hydroxy-3-methoxybenzaldehyde and 2-(3,4-Methylenedioxyphenyl) ethylamine [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(3): 65-73.
[9] ZHENG Qing-si, LIN Mei-fang, TANG Huang. Synthesis of N-Methyl Moxifloxacin Hydrochloride and Its Application in Production [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(2): 101-105.
[10] WU Rui, ZHANG Nan-xi, ZHANG Xiao. Synthesis,Structural Characterization and Magnetic Property of Cu[N(CH2OH)2CH2O](SCN) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(4): 78-83.
[11] HUA Shi-xian, WANG Ying-chun, LI Ya-jun, WANG Heng-shan. Synthesis and Optical Properties of 12-Aryl Substituted Derivatives of Methyl Dehydroabietate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 64-68.
[12] ZENG Jian-qiang, LIANG Guang-ming, HUANG Ying-da, YANG Kun-guo, GUI Liu-cheng, NI Qing-ling. Hydrogen-bonding Directed Three-dimensional Supramolecular Structure in Catena-((μ2-4,4'-bipyridine)-tetraaqua-cobalt(Ⅱ) bis (2-methylbenzimidazolium-1,3-diacetate) dehydrate): Synthesis and Crystal Structural Characterization [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 69-75.
[13] SHENG Liang-bing, SHEN Yan-ling, XIONG Bo-pi, ZOU Hua-hong, LIANG Fu-pei. Synthesis,Crystal Structure and Magnetic Properties of [Mn3(oba)3(DMF)4] [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 76-80.
[14] CHEN Si-yuan, YANG Yang, PENG Yan, LIU Yan-cheng. Crystal Structure and Antitumor Activity of a New Schiff Base Palladium Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 81-86.
[15] ZHANG Zhong, HU Kun, LIN Xin-liang, SUN Ying-ying. Synthesis,Crystal Structure and Spectroscopic Studies of 2-[2-(1H- 1,2,4-Trizole-1-yl)ethyl]-1H-Benzimidazole Hemihydrate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(1): 57-61.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed   
No Suggested Reading articles found!