Design, synthesis and properties investigation of N-acylation lysine based derivatives

被引:1
|
作者
Shi, Ting-Ting [1 ,2 ]
Fang, Zheng [1 ]
Zeng, Wen-Bo [1 ]
Yang, Zhao [3 ]
He, Wei [1 ]
Guo, Kai [1 ,4 ]
机构
[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Jiangsu, Peoples R China
[2] Bengbu Med Coll, Dept Chem, Bengbu 233030, Peoples R China
[3] China Pharmaceut Univ, Sch Engn, 639 Longmian Ave, Nanjing 211198, Jiangsu, Peoples R China
[4] Nanjing Tech Univ, State Key Lab Mat Oriented Chem Engn, Nanjing 211816, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
AMINO-ACID SURFACTANTS; AGGREGATION PROPERTIES; BIOLOGICAL-PROPERTIES; CATIONIC SURFACTANTS; IONIC LIQUIDS; MICELLIZATION; AMPHIPHILES; ADSORPTION; BEHAVIOR;
D O I
10.1039/c9ra00213h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Amino acid-based compounds have attracted attention as environmentally friendly bio-based materials. Our group has recently developed a novel family of N-acylation lysine based derivatives. We introduced long chain acyl groups at the N position selectively by a new synthetic route that avoided the process of amino protection and deprotection. Sodium N-octanamide lysine (C8), sodium N-capramide lysine (C10) and sodium N-lauramide lysine (C12) can self-assemble into vesicles spontaneously. As a result, not only do they have potential in drug delivery system but also they may be used as bio-based surfactants applied in cosmetics and other industries.
引用
收藏
页码:7587 / 7593
页数:7
相关论文
共 50 条
  • [41] Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation
    Yang, Xiaoyu
    Wang, Liang
    Hu, Fangzhi
    Xu, Lubin
    Li, Sanming
    Li, Shuai-Shuai
    ORGANIC LETTERS, 2021, 23 (02) : 358 - 364
  • [42] Synthesis of tropocryptands having heteroatoms in linker chains:: A new class of macrobicyclic ligands derived by N-acylation and N-alkylation of tropocoronand
    Sato, O
    Ono, Y
    Tsunetsugu, J
    HETEROCYCLES, 2002, 57 (11) : 2107 - 2114
  • [43] Design, synthesis and biological evaluation of novel L-lysine ureido derivatives as aminopeptidase N inhibitors
    Su, Li
    Fang, Hao
    Yang, Kanghui
    Xu, Yingying
    Xu, Wenfang
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (02) : 900 - 906
  • [44] Synthesis of 1,3,5-trisubstituted-1,2,4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides
    Lee, Jongbok
    Hong, Myengchan
    Jung, Yoonchul
    Cho, Eun Jin
    Rhee, Hakjune
    TETRAHEDRON, 2012, 68 (08) : 2045 - 2051
  • [45] A convenient method for the N-acylation and esterification of hindered amino acids:: Synthesis of ultra short acting opioid agonist, remifentanil
    Coleman, MJ
    Goodyear, MD
    Latham, DWS
    Whitehead, AJ
    SYNLETT, 1999, (12) : 1923 - 1924
  • [46] Novel acylation catalysts in peptide synthesis:: derivatives of N-hydroxytriazoles and N-hydroxytetrazoles
    Spetzler, JC
    Meldal, M
    Felding, J
    Vedso, P
    Begtrup, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (10): : 1727 - 1732
  • [47] One-Pot Reductive Amination/N-Acylation/Aza-Wittig Reaction for the Synthesis of 3,4-Dihydroquinazolines
    Zhang Wensheng
    Zheng Wei
    Zuo Guoqiang
    Ma Keyou
    Xiao Hequan
    Liu Gaiyun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (05) : 1686 - 1690
  • [48] Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)
    Abbasi, Fatemeh
    Sardarian, Ali Reza
    SCIENTIFIC REPORTS, 2024, 14 (01)
  • [49] One-Pot Diastereoselective Synthesis of Pyrrolopiperazine-2,6-diones by a Ugi/Nucleophilic Substitution/N-Acylation Sequence
    Gonzalez-Saiz, Beatriz
    Carreira-Barral, Israel
    Pertejo, Pablo
    Gomez-Ayuso, Javier
    Quesada, Roberto
    Garcia-Valverde, Maria
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (14): : 9391 - 9398
  • [50] Design and synthesis of new bradykinin antagonists with N-terminal acylation
    Prahl, A
    Wierzba, T
    Wszedybyl, M
    Juzwa, W
    Lammek, B
    POLISH JOURNAL OF CHEMISTRY, 1997, 71 (07) : 915 - 922