Synthesis, Conformational Analysis and Biological Studies of Cyclic Cationic Antimicrobial Peptides Containing Sugar Amino Acids

被引:31
|
作者
Chakraborty, Tushar Kanti [1 ]
Koley, Dipankar [1 ]
Ravi, Rapolu [1 ]
Krishnakumari, Viswanatha [2 ]
Nagaraj, Ramakrishnan [2 ]
Kunwar, Ajit Chand [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500607, Andhra Pradesh, India
[2] Ctr Cellular & Mol Biol, Hyderabad 500607, Andhra Pradesh, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期
关键词
D O I
10.1021/jo801123q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sugar amino acid based 24-membered macrocycliC C-2-symmetric cationic peptides were designed and synthesized. The cationic group was introduced in the sugar amino acids. The conformation of these cyclic compounds was ascertained through NMR techniques, which proved they were amphipathic in nature. All the compounds were bacteriolytic, showed good activity against the Gr(+v)e and Gr(-ve) bacteria, and exhibited low hemolytic activity.
引用
收藏
页码:8731 / 8744
页数:14
相关论文
共 50 条
  • [21] Conformational properties of peptides containing dehydro amino acids
    Thormann, M
    Hofmann, HJ
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1998, 431 (1-2): : 79 - 96
  • [22] Synthesis and conformational studies of peptidomimetics containing furanoid sugar amino acids and a sugar diacid (vol 65, pg 6441, 2000)
    Chakraborty, TK
    Ghosh, S
    Jayaprakash, S
    Sarna, JARP
    Ravikanth, V
    Diwan, PV
    Nagaraj, R
    Kunwar, AC
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22): : 7710 - 7710
  • [23] Synthesis of cyclic dipeptide templates, their incorporation into peptides and studies on their conformational and biological properties
    Asche, G
    Kunz, H
    Nar, H
    Köppen, H
    Briem, H
    Pook, KH
    Schiller, PW
    Chung, NN
    Lemieux, C
    Esser, F
    JOURNAL OF PEPTIDE RESEARCH, 1998, 51 (05): : 323 - 336
  • [24] Cyclic peptides containing a δ-sugar amino acid-synthesis and evaluation as artificial receptors
    Billing, JF
    Nilsson, UJ
    TETRAHEDRON, 2005, 61 (04) : 863 - 874
  • [25] Synthesis of peptides containing oxo amino acids and their crystallographic analysis
    Kalita, Mrinal
    Archana, Archana
    Dimri, Astha
    Vasudev, Prema G.
    Ramapanicker, Ramesh
    JOURNAL OF PEPTIDE SCIENCE, 2019, 25 (03)
  • [26] Synthesis and conformational analysis of β-amino acid-derived small cyclic peptides
    Rajesh, B. M.
    Kumar, S. Kiran
    Kunwar, Ajit Chand
    Iqbal, Javed
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3276 - U3276
  • [27] SYNTHETIC STUDIES TOWARDS CYCLIC-PEPTIDES - CONCISE SYNTHESIS OF THIAZOLINE AND THIAZOLE CONTAINING AMINO-ACIDS
    NORTH, M
    PATTENDEN, G
    TETRAHEDRON, 1990, 46 (24) : 8267 - 8290
  • [28] Folded conformation in peptides containing furanoid sugar amino acids
    Chakraborty, T.K.
    Jayaprakash, S.
    Diwan, P.V.
    Nagaraj, R.
    Jampani, S.R.B.
    Kunwar, A.C.
    Journal of the American Chemical Society, 1998, 120 (51):
  • [29] Folded conformation in peptides containing furanoid sugar amino acids
    Chakraborty, TK
    Jayaprakash, S
    Diwan, PV
    Nagaraj, R
    Jampani, SRB
    Kunwar, AC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) : 12962 - 12963
  • [30] Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides
    Remond, Emmanuelle
    Martin, Charlotte
    Martinez, Jean
    Cavelier, Florine
    CHEMICAL REVIEWS, 2016, 116 (19) : 11654 - 11684