Synthesis and Self-Assembly of Bolaamphiphiles Based on β-Amino Acids or an Alcohol

被引:5
作者
Mainkar, Prathama S. [1 ]
Sridhar, Chirumarry [1 ]
Sudhakar, Ambadi [1 ]
Chandrasekhar, Srivari [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
Bolaamphiphiles; Self-assembly; Amino acids; Glycosides; AZT; Norbornenes; CARBOXYLIC-ACIDS; OLIGOMERS; 14-HELIX; GELATORS; PEPTIDE;
D O I
10.1002/hlca.201200060
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of bolaamphiphiles from unusual beta-amino acids or an alcohol and C12 or C20 spacers is described. Unusual beta-amino acids such as a sugar amino acid, an AZT-derived amino acid, a norbornene amino acid, and an AZT-derived amino alcohol were coupled with spacers under standard conditions to get the novel bolaamphiphiles 58 (Scheme 1), 12 and 13 (Scheme 2), and 17 and 20 (Scheme 3). Some of these compounds, on precipitation from MeOH/H2O, self-assembled into organized molecular structures.
引用
收藏
页码:99 / 108
页数:10
相关论文
共 50 条
[41]   Vesicles from the self-assembly of the ultra-small fatty acids with amino acids under aqueous conditions [J].
Chen, Li-Chun ;
Chen, Ke-Xian ;
Huang, Xi-ying ;
Lou, Jian ;
Li, Jing-Yuan ;
Deng, Shao-Ping .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2019, 173 :69-76
[42]   Formation of a Double Diamond Cubic Phase by Thermotropic Liquid Crystalline Self-Assembly of Bundled Bolaamphiphiles [J].
Zeng, Xiangbing ;
Prehm, Marko ;
Ungar, Goran ;
Tschierske, Carsten ;
Liu, Feng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (29) :8324-8327
[43]   Self-Assembly in Protein-Based Bionanomaterials [J].
Solomonov, Aleksei ;
Shimanovich, Ulyana .
ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (12) :1152-1170
[44]   Design, Synthesis and Self-Assembly of Functional Amphiphilic Metallodendrimers [J].
Neranon, Kitjanit ;
Alberch, Laura ;
Ramstrom, Olof .
CHEMISTRYOPEN, 2020, 9 (01) :45-52
[45]   Synthesis and Self-assembly Behavior of Porphyrin-based Polypeptides [J].
Wang, Yin-chao ;
Zheng, Jia-hao ;
Zhang, Wei-an ;
Cai, Chun-hua ;
Lin, Jia-ping .
ACTA POLYMERICA SINICA, 2024, 55 (02) :172-181
[46]   Synthesis, self-assembly and applications of functional polymers based on porphyrins [J].
Tian, Jia ;
Zhang, Weian .
PROGRESS IN POLYMER SCIENCE, 2019, 95 :65-117
[47]   Metal array fabrication through self-assembly of Pt-complex-bound amino acids [J].
Isozaki, Katsuhiro ;
Ogata, Kazuki ;
Haga, Yusuke ;
Sasano, Daisuke ;
Ogawa, Tetsuya ;
Kurata, Hiroki ;
Nakamura, Masaharu ;
Naota, Takeshi ;
Takaya, Hikaru .
CHEMICAL COMMUNICATIONS, 2012, 48 (33) :3936-3938
[48]   Self-assembly of a peptide sequence, EKKE, composed of exclusively charged amino acids: Role of charge in morphology and lead binding [J].
Natarajan, Aishwarya ;
Rangan, Krishnan ;
Vadrevu, Ramakrishna .
JOURNAL OF PEPTIDE SCIENCE, 2023, 29 (02)
[49]   A self-standing superhydrophobic material formed by the self-assembly of an individual amino acid [J].
Hu, Tan ;
Zhang, Zhuo ;
Reches, Meital .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2024, 655 :899-908
[50]   Conformational and self-assembly studies of helix forming hexapeptides containing two α-amino isobutyric acids [J].
Dutt, Anita ;
Drew, Michael G. B. ;
Pramanik, Animesh .
TETRAHEDRON, 2008, 64 (03) :549-558