Pseudo-A(1,3) strain as a key conformational control element in the design of poly-L-proline type II peptide mimics

被引:47
作者
Zhang, R [1 ]
Brownewell, F [1 ]
Madalengoitia, JS [1 ]
机构
[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA
关键词
D O I
10.1021/ja972494e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A strategy for the synthesis of peptide mimics of the poly-L-proline type II secondary structure from 4-substituted prolines is presented. Dimeric and trimeric oligomers composed of 3-substituted prolines are shown by NMR to preferentially populate the poly-L-proline type II secondary structure in both CDCl3 and D2O. Oligomers composed of 4-substituted prolines thus imitate the desired backbone conformation and are able to incorporate non-prolyl side chains on the proline backbone.
引用
收藏
页码:3894 / 3902
页数:9
相关论文
共 22 条
  • [1] LEFT-HANDED POLYPROLINE-II HELICES COMMONLY OCCUR IN GLOBULAR-PROTEINS
    ADZHUBEI, AA
    STERNBERG, MJE
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 1993, 229 (02) : 472 - 493
  • [2] AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL
    BALDWIN, JE
    MIRANDA, T
    MOLONEY, M
    HOKELEK, T
    [J]. TETRAHEDRON, 1989, 45 (23) : 7459 - 7468
  • [3] CUNG MT, 1987, NEW J CHEM, V11, P503
  • [4] STERIC EFFECTS OF CIS-TRANS ISOMERISM ON NEIGHBORING RESIDUES IN PROLINE OLIGOPEPTIDES - C-13-NMR STUDY OF CONFORMATIONAL HETEROGENEITY IN LINEAR TRIPEPTIDES
    DESLAURIERS, R
    BECKER, JM
    STEINFELD, AS
    NAIDER, F
    [J]. BIOPOLYMERS, 1979, 18 (03) : 523 - 538
  • [5] SYNTHESIS OF ENANTIOMERICALLY PURE 4-SUBSTITUTED GLUTAMIC ACIDS AND PROLINES - GENERAL ALDOL REACTION OF PYROGLUTAMATE LACTAM LITHIUM ENOLATE MEDIATED BY ET(2)O-CENTER-DOT-BF3
    EZQUERRA, J
    PEDREGAL, C
    YRURETAGOYENA, B
    RUBIO, A
    CARRENO, MC
    ESCRIBANO, A
    RUANO, JLG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) : 2925 - 2930
  • [6] STEREOSELECTIVE REACTIONS OF LITHIUM ENOLATES DERIVED FROM N-BOC PROTECTED PYROGLUTAMIC ESTERS
    EZQUERRA, J
    PEDREGAL, C
    RUBIO, A
    YRURETAGOYENA, B
    ESCRIBANO, A
    SANCHEZFERRANDO, F
    [J]. TETRAHEDRON, 1993, 49 (38) : 8665 - 8678
  • [7] 2 BINDING ORIENTATIONS FOR PEPTIDES TO THE SRC SH3 DOMAIN - DEVELOPMENT OF A GENERAL-MODEL FOR SH3-LIGAND INTERACTIONS
    FENG, SB
    CHEN, JK
    YU, HT
    SIMON, JA
    SCHREIBER, SL
    [J]. SCIENCE, 1994, 266 (5188) : 1241 - 1247
  • [8] Specific interactions outside the proline-rich core of two classes of Src homology 3 ligands
    Feng, SB
    Kasahara, C
    Rickles, RJ
    Schreiber, SL
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (26) : 12408 - 12415
  • [9] Structure of the p53 tumor suppressor bound to the ankyrin and SH3 domains of 53BP2
    Gorina, S
    Pavletich, NP
    [J]. SCIENCE, 1996, 274 (5289) : 1001 - 1005
  • [10] Crystallographic analysis of endogenous peptides associated with HLA-DR1 suggests a common, polyproline II-like conformation for bound peptides
    Jardetzky, TS
    Brown, JH
    Gorga, JC
    Stern, LJ
    Urban, RG
    Strominger, JL
    Wiley, DC
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (02) : 734 - 738