c[D-pro-Pro-D-pro-N-methyl-Ala] adopts a rigid conformation that serves as a scaffold to mimic reverse-turns.
c[D-pro-Pro-D-pro-N-methyl-Ala] adopts a rigid conformation that serves as a scaffold to mimic reverse-turns.
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c[D-pro-Pro-D-pro-N-methyl-Ala] 采用刚性构象作为模拟回旋的支架。
DOI：
10.1002/bip.20869
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发表时间：
2008
期刊：
影响因子：
2.9
通讯作者：
Marshall,GarlandR
中科院分区：
文献类型：
--
作者：
Arbor,Sage;Kao,Jeff;Wu,Yun;Marshall,GarlandR
Naturally occurring cyclic tetrapeptides (CTPs) such as tentoxin (Halloin et al., Plant Physiol 1970, 45, 310–314; Saad, Phytopathology 1970, 60, 415–418), ampicidin (Darkin‐Rattray, Proc Natl Acad Sci USA 1996, 93, 13143–13147), HC‐toxin (Walton, Proc Natl Acad Sci USA 1987, 84, 8444–8447), and trapoxin (Yoshida and Sugita, Jpn J Cancer Res 1992, 83, 324–328; Itazaki et al., J Antibiot (Tokyo) 1990, 43, 1524–1532) have a wide range of biological activity and potential use ranging from herbicides (Walton, Proc Natl Acad Sci USA 1987, 84, 8444–8447; Judson, J Agric Food Chem 1987, 35, 451–456) to therapeutics (Loiseau, Biopolymers 2003, 69, 363–385) for malaria (Darkin‐Rattray, Proc Natl Acad Sci USA 1996, 93, 13143–13147) and cancer (Yoshida and Sugita, Jpn J Cancer Res 1992, 83, 324–328). To elucidate scaffolds that have few low‐energy conformations and could serve as semirigid reverse‐turn mimetics, the flexibility of CTPs was determined computationally. Four analogs of cyclic tetraproline c[Pro‐pro‐Pro‐pro] with alternatingL‐ andD‐prolines, namely c[pro‐Pro‐pro‐NMe‐Ala], c[pip‐Pro‐pip‐Pro], c[pro‐Pip‐pro‐Pro], and c[Ala‐Pro‐pip‐Pro] were synthesized and characterized by NOESY NMR. Both molecular mechanics and Density Functional Theory quantum calculations found these head‐to‐tail CTPs to be constrained to one or two relatively stable conformations. NMR structures, while not always yielding the same lowest energy conformation as expected by in silico predictions, confirmed only one or two highly populated solution conformations for all four peptides examined. c[pro‐Pro‐pro‐NMe‐Ala] was shown to have a single alltrans‐amide bond conformation from both in silico predictions and NMR characterization, and to be a reverse‐turn mimetic by overlapping four Cα‐Cβ bonds with those for ∼6.5% (Tran, J Comput Aided Mol Des 2005, 19, 551–566) of reverse‐turns in the Protein Data Bank PDB with a RMSD of 0.57 Å. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90: 384–393, 2008.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com
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