学术探索
学术期刊
新闻热点
数据分析
智能评审

An unusual reverse turn structure adopted by a furanoid sugar amino acid incorporated in gramicidin S

被引：96
作者：
Grotenbreg, GM
Timmer, MSM
Llamas-Saiz, AL
Verdoes, M
van der Marel, GA
van Raaij, MJ
Overkleeft, HS
Overhand, M
机构：
[1] Leiden Inst Chem, Gorlaeus Labs, NL-2300 RA Leiden, Netherlands
[2] Univ Santiago, RIAIDT, Lab Integral Dinam & Estruct Biomol Jose R Carrac, Edif CACTUS, Santiago De Compostela 15782, Spain
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 11期
关键词：
D O I：
10.1021/ja0397254
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new reverse turn, replacing one of the native type II′ β-turns in the cyclic peptide antibiotic gramicidin S, induced by a furanoid sugar amino acid is revealed. The C3-hydroxyl function plays a pivotal role by acting as a H-bond acceptor, consequently flipping the amide bond between residues i and i + 1, as was established by NMR and X-ray crystallographic analysis. Copyright © 2004 American Chemical Society.
引用
收藏
页码：3444 / 3446
页数：3
相关论文
共 51 条
  • [1] Aguilera B, 2001, EUR J ORG CHEM, V2001, P1541, DOI 10.1002/1099-0690(200104)2001:8<1541::AID-EJOC1541>3.0.CO
  • [2] 2-7
  • [3] CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - NEW DESCRIPTION USING CONCEPT OF PSEUDOROTATION
    ALTONA, C
    SUNDARALINGAM, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (23) : 8205 - +
  • [4] IBTM-containing gramicidin S analogues: Evidence for IBTM as a suitable type II' beta-turn mimetic
    Andreu, D
    Ruiz, S
    Carreno, C
    Alsina, J
    Albericio, F
    Jimenez, MA
    delaFiguera, N
    Herranz, R
    GarciaLopez, MT
    GonzalezMuniz, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10579 - 10586
  • [5] Arndt HD, 2002, ANGEW CHEM INT EDIT, V41, P4062, DOI 10.1002/1521-3773(20021104)41:21<4062::AID-ANIE4062>3.0.CO
  • [6] 2-U
  • [7] BACH AC, 1991, INT J PEPT PROT RES, V38, P314
  • [8] Bioinspired polymeric materials: in-between proteins and plastics
    Barron, AE
    Zuckermann, RN
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (06) : 681 - 687
  • [9] CASTRO B, 1975, TETRAHEDRON LETT, P1219
  • [10] Synthesis and conformational studies by peptidomimetics containing furanoid sugar amino acids an a sugar diacid
    Chakraborty, TK
    Ghosh, S
    Jayaprakash, S
    Sharma, JARP
    Ravikanth, V
    Diwan, PV
    Nagaraj, R
    Kunwar, AC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) : 6441 - 6457
123456