| Title | An Evaluation of Peptide-Bond Isosteres |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Choudhary, A, Raines, RT |
| Journal | Chembiochem |
| Volume | 12 |
| Pagination | 1801-1807 |
| Date Published | Aug |
| Accession Number | WOS:000294268600001 |
| Keywords | Aleman C, 2001, V105, P6717, alkenes, alpha-helices, Amino-acid mutagenesis, Aravinda S, 2002, V64, P255, Artis DR, 1998, V120, P12200, backbone interactions, barrier, Bateman KS, 2001, V305, P839, Bieschke J, 2008, V47, P50, Biochemistry & Molecular Biology, BLOM CE, 1981, V84, P267, BRANDTS JF, 1975, V14, P4953, Choudhary A, 2009, V131, P7244, Choudhary A, 2010, P251, Choudhary A, 2011, V20, P1077, Choudhary A, 2011, V41, P181, collagen triple-helix, conformational-analysis, crystal-structure, DeRider ML, 2002, V124, P2497, esters, fischer e, 1906, fluoroalkenes, Frank R, 2000, V39, P1120, Fu YW, 2006, V128, P15948, Fuller AA, 2009, V106, P11067, Gao JM, 2009, V16, P684, Glendening ED, 1997, V119, P12940, Grabarse WG, 2000, V303, P329, GRAY HB, 1965,, Gung BW, 2008, V73, P689, HARADA I, 1980, V70, P279, Hart SA, 1999, V64, P2998, HEIKE JA, 2007, V119, P7912, Helbing J, 2004, V126, P8823, HINDERAKER CMP, 2003, V12, P1188, Hoffmann RW, 2002, V85, P4424, HOFMEISTER F, 2002, V1, P759, Hollenstein M, 2005, V70, P3205, HOPFER U, 1997, V109, P1805, HUTKOWSKI M, 1995, V34, P13016, HUTZ R, 2000, V112, P1305, hydrogen-bond, JAKOBSCHE CE, 2008, V120, P6809, Jakobsche CE, 2008, V47, P6707, Jakobsche CE, 2010, V132, P6651, Jenkins CL, 2004, V69, P8565, Jenkins CL, 2005, V7, P2619, KALLIES B, 1996, V2, P1397, Karle IL, 2001, V59, P276, KIRBY AJ, 1983,, KITAZUME T, 1998,, Koh JT, 1997, V36, P11314, Langmuir I, 1919, V41, P1543, Lee HJ, 2002, V106, P7010, Min BK, 1998, V471, P283, n-methylthioacetamide, n-pi* interactions, Ohyama T, 2000, V54, P375, Ohyama T, 2001, V58, P636, PERCZEL A, 1991, V113, P6256, Pharmacology & Pharmacy, POWERS ET, 2005, V72, P39, Radzicka A, 1996, V118, P6105, RAMAKRISHNAN C, 1978, V87, P13, Reiner A, 2008, V130, P8079, rotational, Satzger H, 2005, V109, P4770, Scheike JA, 2007, V46, P7766, Scheiner S, 2001, V105, P10607, Schutz R, 2000, V39, P1250, secondary structure, Slongchamps ap, 1977, v7, p1271, Slongchamps cp, 1980, v58, p1051, thioamides, Toth G, 2004, V108, P9287, Tran TT, 2001, V20, P245, Tran TT, 2001, V22, P1010, Wang XDJ, 2006, V84, P125, WEBER AL, 1981, V17, P273, Weinhold F, 2006, V72, P121, WIBERG KB, 1987, V109, P5935, Wiberg KB, 2001, V123, P2038, Wipf P, 1998, V63, P6088, Wipf P, 2005, V347, P1605, Xiao JB, 2005, V127, P5742, YANG AS, 1995, V252, P351, Zhao JZ, 2003, P2810 |
| Abstract | Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partake in noncovalent interactions is compared with that of the peptide bond. The consequential perturbations provide a useful tool for chemical biologists to reveal new structure-function relationships, and to endow peptides and proteins with desirable attributes.
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| Short Title | Chembiochem |
