Synthesis of AApeptides

Methods in Molecular Biology

Volumn 1081, Issue , 2013, Pages 35-46

  Niu, Youhong ^a   Hu, Yaogang ^a   Wu, Haifan ^a   Cai, Jianfeng ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Cyclization; Lipidation; Solid phase synthesis; AApeptides; AApeptides

Indexed keywords

AAPEPTIDE; AMYLOID BETA PROTEIN; AZAPEPTIDE; NANOMATERIAL; OLIGOMER; PEPTIDE DERIVATIVE; PEPTIDOMIMETIC AGENT; PEPTOID; POLYAMIDE; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTIMICROBIAL ACTIVITY; ARTICLE; CHIRALITY; CONTROLLED STUDY; CYCLIZATION; PEPTIDE SYNTHESIS; PEPTIDOMICS; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN FOLDING; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE; SEQUENCE ANALYSIS; SOLID PHASE EXTRACTION;

CYCLIZATION; PEPTIDES; PEPTIDOMIMETICS; SOLID-PHASE SYNTHESIS TECHNIQUES;

EID: 84934437415     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-62703-652-8_3     Document Type: Article

References (35)

1. Wu Y-D, Gellman S (2008) Peptidomimetics. Acc Chem Res 41:1231-1232
2. Tuwalska D, Sienkiewicz J, Liberek B (2008) Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides. Carbohydr Res 343:1142-1152
3. Risseeuw MD, Mazurek J, van Langenvelde A, van der Marel GA, Overkleeft HS, Overhand M (2007) Synthesis of alkylated sugar amino acids: conformationally restricted L-Xaa-L-Ser/Thr mimics. Org Biomol Chem 5:2311-2314
4. Horne WS, Johnson LM, Ketas TJ, Klasse PJ, Lu M, Moore JP, Gellman SH (2009) Structural and biological mimicry of protein surface recognition by alpha/beta-peptide foldamers. Proc Natl Acad Sci USA 106: 14751-14756
5. Horne WS, Gellman SH (2008) Foldamers with heterogeneous backbones. Acc Chem Res 41:1399-1408
6. Dervan PB (1986) Design of sequencespecific DNA-binding molecules. Science 232: 464-471
7. Simon RJ, Kania RS, Zuckermann RN, Huebner VD, Jewell DA, Banville S, Ng S, Wang L, Rosenberg S, Marlowe CK et al (1992) Peptoids: a modular approach to drug discovery. Proc Natl Acad Sci USA 89: 9367-9371
8. Cheng RP, Gellman SH, DeGrado WF (2001) beta-Peptides: from structure to function. Chem Rev 101:3219-3232
9. Seebach D, Ciceri PE, Overhand M, Jaun B, Rigo D, Oberer L, Hommel U, Amstutz R, Widmer H (1996) Probing the helical secondary structure of short-chain beta-peptides. Helv Chim Acta 79:2043-2066
10. Kritzer JA, Stephens OM, Guarracino DA, Reznik SK, Schepartz A (2005) beta-Peptides as inhibitors of protein-protein interactions. Bioorg Med Chem 13:11-16
11. Kumbhani DJ, Sharma GV, Khuri SF, Kirdar JA (2006) Fascicular conduction disturbances after coronary artery bypass surgery: a review with a meta-analysis of their long-term significance. J Card Surg 21:428-434
12. Arndt HD, Ziemer B, Koert U (2004) Folding propensity of cyclohexylether-delta-peptides. Org Lett 6:3269-3272
13. Trabocchi A, Guarna F, Guarna A (2005) gamma- and delta-Amino acids: synthetic strategies and relevant applications. Curr Org Chem 9:1127-1153
14. Violette A, Petit MC, Rognan D, Monteil H, Guichard G (2005) Oligourea foldamers as antimicrobial peptidomimetics. Biopolymers 80:516
15. Boeijen A, van Ameijde J, Liskamp RMJ (2001) Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy. J Org Chem 66:8454-8462
16. Lee HJ, Song JW, Choi YS, Park HM, Lee KB (2002) A theoretical study of conformational properties of N-methyl azapeptide derivatives. J Am Chem Soc 124:11881-11893
17. Graybill TL, Ross MJ, Gauvin BR, Gregory JS, Harris AL, Ator MA, Rinker JM, Dolle RE (1992) Synthesis and evaluation of azapeptide-derived inhibitors of serine and cysteine proteases. Bioorg Med Chem Lett 2: 1375-1380
18. Li X, Wu YD, Yang D (2008) Alpha-aminoxy acids: new possibilities from foldamers to anion receptors and channels. Acc Chem Res 41:1428-1438
19. Nelson JC, Saven JG, Moore JS, Wolynes PG (1997) Solvophobically driven folding of nonbiological oligomers. Science 277:1793-1796
20. Patch JA, Barron AE (2002) Mimicry of bioactive peptides via non-natural, sequencespecific peptidomimetic oligomers. Curr Opin Chem Biol 6:872-877
21. Gellman S (2009) Structure and function in peptidic foldamers. Biopolymers 92:293
22. Goodman CM, Choi S, Shandler S, DeGrado WF (2007) Foldamers as versatile frameworks for the design and evolution of function. Nat Chem Biol 3:252-262
23. Niu Y, Padhee S, Wu H, Bai G, Harrington L, Burda WN, Shaw LN, Cao C, Cai J (2011) Identification of gamma-AApeptides with potent and broad-spectrum antimicrobial activity. Chem Commun (Camb) 47: 12197-12199
24. Niu Y, Jones AJ, Wu H, Varani G, Cai J (2011) gamma-AApeptides bind to RNA by mimicking RNA-binding proteins. Org Biomol Chem 9:6604-6609
25. Padhee S, Hu Y, Niu Y, Bai G, Wu H, Costanza F, West L, Harrington L, Shaw LN, Cao C, Cai J (2011) Non-hemolytic alpha-AApeptides as antimicrobial peptidomimetics. Chem Commun (Camb) 47:9729-9731
26. Niu Y, Hu Y, Li X, Chen J, Cai J (2011) [gamma]-AApeptides: design, synthesis and evaluation. New J Chem 35:542-545
27. Niu Y, Padhee S, Wu H, Bai G, Qiao Q, Hu Y, Harrington L, Burda WN, Shaw LN, Cao C, Cai J (2012) Lipo-gamma-AApeptides as a new class of potent and broad-spectrum antimicrobial agents. J Med Chem 55: 4003-4009
28. Bai G, Padhee S, Niu Y, Wang RE, Qiao Q, Buzzeo R, Cao C, Cai J (2012) Cellular uptake of an alpha-AApeptide. Org Biomol Chem 10:1149-1153
29. Niu Y, Bai G, Wu H, Wang RE, Qiao Q, Padhee S, Buzzeo R, Cao C, Cai J (2012) Cellular translocation of a gamma-AApeptide mimetic of Tat peptide. Mol Pharm 9:1529-1534
30. Hu Y, Li X, Sebti SM, Chen J, Cai J (2011) Design and synthesis of AApeptides: a new class of peptide mimics. Bioorg Med Chem Lett 21:1469-1471
31. Niu Y, Wu H, Huang R, Qiao Q, Constanza F, Wang X, Hu Y, Amin MN, Naguyen A, Zhang J, Haller E, Ma S, Li X, Cai J (2012) Nanorods formed from a new class of peptidomimetics. Macromolecules. doi: 10.1021/ma3015992
32. Hu Y, Amin MN, Padhee S, Wang R, Qiao Q, Ge B, Li Y, Mathew A, Cao C, Cai J (2012) Lipidated peptidomimetics with improved antimicrobial activity. ACS Med Chem Lett 3:683-686
33. Wu H, Niu Y, Padhee S, Wang RE, Li Y, Qiao Q, Ge B, Cao C, Cai J (2012) Design and synthesis of unprecedented cyclic gamma-AApeptides for antimicrobial development. Chem Sci 3:2570-2575
34. Debaene F, Da Silva JA, Pianowski Z, Duran FJ, Winssinger N (2007) Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases. Tetrahedron 63: 6577-6586
35. Debaene F, Mejias L, Harris JL, Winssinger N (2004) Synthesis of a PNA-encoded cysteine protease inhibitor library. Tetrahedron 60:8677-8690