Probing dipeptide trans/cis stereochemistry using pH control of thiopeptide analogues, and application to the PepT1 transporter

被引:14
作者
Bailey, PD
Boyd, CAR
Collier, ID
Kellett, GL
Meredith, D
Morgan, KM
Pettecrew, R
Price, RA
机构
[1] Univ Manchester, Sch Chem, Manchester M60 1QD, Lancs, England
[2] Univ Oxford, Dept Human Anat & Genet, Oxford OX1 3QX, England
[3] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland
[4] Univ York, Dept Biol Area 3, York YO1 5DD, N Yorkshire, England
基金
英国惠康基金;
关键词
D O I
10.1039/b513274f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereochemistry of thiodipeptides of proline [e.g. Ala-psi[CS-N]-Pro] can be controlled using pH, allowing the trans-preference for substrates of the peptide transporter PepT1 to be confirmed.
引用
收藏
页码:4038 / 4039
页数:2
相关论文
共 10 条
[1]   Evidence for the absolute conformational specificity of the intestinal H+/peptide symporter, PEPT1 [J].
Brandsch, M ;
Thunecke, F ;
Küllertz, G ;
Schutkowski, M ;
Fischer, G ;
Neubert, K .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (07) :3861-3864
[2]   Molecular and integrative physiology of intestinal peptide transport [J].
Daniel, H .
ANNUAL REVIEW OF PHYSIOLOGY, 2004, 66 :361-384
[3]   Insights into the catalytic mechanism of peptidyl prolyl cis/trans isomerases [J].
Fanghänel, J ;
Fischer, G .
FRONTIERS IN BIOSCIENCE-LANDMARK, 2004, 9 :3453-3478
[4]  
FANGHANEL J, ANGEW CHEM INT ED, V42, P490
[5]   Regulation of peptide bond cis/trans isomerization by enzyme catalysis and its implication in physiological processes [J].
Fischer, G ;
Aumüller, T .
REVIEWS OF PHYSIOLOGY, BIOCHEMISTRY AND PHARMACOLOGY, VOL 148, 2004, 148 :105-150
[6]  
MAISON W, 2004, HIGHLIGHTS BIOORG CH, P29
[7]   4-aminomethylbenzoic acid is a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1 [J].
Meredith, D ;
Boyd, CAR ;
Bronk, JR ;
Bailey, PD ;
Morgan, KM ;
Collier, ID ;
Temple, CS .
JOURNAL OF PHYSIOLOGY-LONDON, 1998, 512 (03) :629-634
[8]   Structure and function of eukaryotic peptide transporters [J].
Meredith, D ;
Boyd, CAR .
CELLULAR AND MOLECULAR LIFE SCIENCES, 2000, 57 (05) :754-778
[9]   Probing substrate backbone function in prolyl oligopeptidase catalysis - Large positional effects of peptide bond monothioxylation [J].
Schutkowski, M ;
Jakob, M ;
Landgraf, G ;
Born, I ;
Neubert, K ;
Fischer, G .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1997, 245 (02) :381-385
[10]   Peptide transporters: Structure, function, regulation and application for drug delivery [J].
Terada, T ;
Inui, K .
CURRENT DRUG METABOLISM, 2004, 5 (01) :85-94