Extraordinary metabolic stability of peptides containing α-aminoxy acids

Amino Acids

Volumn 43, Issue 1, 2012, Pages 499-503

  Chen, Fei ^a   Ma, Bin ^b   Yang, Zong Chang ^a   Lin, Ge ^b   Yang, Dan ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Aminoxy acid; Metabolism; Peptides; Stability

Indexed keywords

ALPHA AMINO ACID; ALPHA AMINOXY ACID DERIVATIVE; MOLECULAR SCAFFOLD; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDE BOND; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; DRUG DESIGN; PRIORITY JOURNAL; PROTEIN METABOLISM; PROTEIN STABILITY; PROTEIN STRUCTURE;

AMINO ACIDS; ANIMALS; MICROSOMES, LIVER; PEPTIDES; PROTEIN STABILITY; PROTEIN STRUCTURE, SECONDARY; RATS;

EID: 84862768277     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-1095-8     Document Type: Article

References (25)

1. AD Bautista CJ Craig EA Harker A Schepartz 2007 Sophistication of foldamer form and function in vitro and in vivo Curr Opin Chem Biol 11 6 685 692 10.1016/j.cbpa.2007.09.009 17988934 10.1016/j.cbpa.2007.09.009 1:CAS:528:DC%2BD2sXhtlyrtbvL (Pubitemid 350180570)
2. F Chen NY Zhu D Yang 2004 Gamma(4)-aminoxy peptides as new peptidomimetic foldamers J Am Chem Soc 126 49 15980 15981 10.1021/Ja044493 15584729 10.1021/ja044493+ 1:CAS:528:DC%2BD2cXpvFWjuro%3D (Pubitemid 39627606)
3. F Chen KS Song YD Wu D Yang 2008 Synthesis and conformational studies of gamma-aminoxy peptides J Am Chem Soc 130 2 743 755 10.1021/Ja0772750 18088122 10.1021/ja0772750 1:CAS:528:DC%2BD2sXhsVemtrrK (Pubitemid 351455588)
4. RP Cheng SH Gellman WF DeGrado 2001 Beta-peptides: from structure to function Chem Rev 101 10 3219 3232 10.1021/Cr000045i 11710070 10.1021/cr000045i 1:CAS:528:DC%2BD3MXntlGntbg%3D (Pubitemid 35377819)
5. J Frackenpohl PI Arvidsson JV Schreiber D Seebach 2001 The outstanding biological stability of beta- and gamma-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases Chembiochem 2 6 445 455 11828476 10.1002/1439-7633(20010601)2:6<445::AID-CBIC445>3.0.CO;2-R 1:CAS:528:DC%2BD3MXksVGjsLc%3D (Pubitemid 33723576)
6. SH Gellman 1998 Foldamers: a manifesto Accounts Chem Res 31 4 173 180 10.1021/ar960298r 1:CAS:528:DyaK1cXhvF2qtr0%3D (Pubitemid 128474551)
7. A Giannis 1993 Peptidomimetics for receptor ligands discovery, development, and medical perspectives Angew Chem Int Ed 32 9 1244 1267 10.1002/anie.199312441
8. D Haldar 2008 Recent developments in the synthesis of amino acids and analogues for foldamers study Curr Org Synth 5 1 61 80 10.2174/ 157017908783497527 1:CAS:528:DC%2BD1cXisVartLo%3D
9. T Heck M Limbach B Geueke M Zacharias J Gardiner HPE Kohler D Seebach 2006 Enzymatic degradation of beta- and mixed alpha, beta-oligopeptides Chem Biodivers 3 12 1325 1348 17193247 10.1002/cbdv.200690136 1:CAS:528: DC%2BD2sXmsFyjsA%3D%3D (Pubitemid 46062513)
10. DJ Hill MJ Mio RB Prince TS Hughes JS Moore 2001 A field guide to foldamers Chem Rev 101 12 3893 4011 10.1021/Cr990120t 11740924 10.1021/cr990120t 1:CAS:528:DC%2BD3MXovFagtrk%3D (Pubitemid 35373050)
11. T Hintermann D Seebach 1997 The biological stability of beta-peptides: no interactions between alpha- and beta-peptidic structures Chimia 51 5 244 247 1:CAS:528:DyaK2sXjvVSmu7k%3D (Pubitemid 127386096)
12. L Kisfaludy I Schon J Nafradi L Varga V Varro 1978 Pentagastrin analogs containing alpha-aminooxy acids: synthesis of analogs substituted at N-terminus H-S Z Physiol Chem 359 8 887 895 10.1515/bchm2.1978.359.2.887 1:CAS:528:DyaE1cXlvFOqt7s%3D (Pubitemid 9060550)
13. M Lee J Lee B Baek I Shin 2003 The first solid-phase synthesis of oligomeric alpha-aminooxy peptides Synlett 3 325 328 1:CAS:528: DC%2BD3sXotVSrt7o%3D (Pubitemid 36269315)
14. Li X, Shen B, Yao XQ, Yang D (2007) A small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes. J of the Am Chem Soc 129 (23):7264-7265. doi: 10.1021/Ja071961h (Pubitemid 46980799)
15. X Li B Shen XQ Yao D Yang 2009 Synthetic chloride channel regulates cell membrane potentials and voltage-gated calcium channels J Am Chem Soc 131 38 13676 13680 10.1021/Ja902352g 19772362 10.1021/ja902352g 1:CAS:528: DC%2BD1MXhtFajsr7J
16. D Seebach JL Matthews 1997 Beta-peptides: a surprise at every turn Chem Commun 21 2015 2022 10.1039/a704933a
17. D Seebach S Abele JV Schreiber B Martinoni AK Nussbaum H Schild H Schulz H Hennecke R Woessner F Bitsch 1998 Biological and pharmacokinetic studies with beta-peptides Chimia 52 12 734 739 1:CAS:528:DyaK1MXis1akug%3D%3D
18. D Yang FF Ng ZJ Li YD Wu KWK Chan DP Wang 1996 An unusual turn structure in peptides containing alpha-aminoxy acids J Am Chem Soc 118 40 9794 9795 10.1021/ja960515j 1:CAS:528:DyaK28XmtF2isbs%3D (Pubitemid 26358348)
19. D Yang J Qu B Li FF Ng XC Wang KK Cheung DP Wang YD Wu 1999 Novel turns and helices in peptides of chiral alpha-aminoxy acids J Am Chem Soc 121 3 589 590 10.1021/ja982528y 1:CAS:528:DyaK1MXhslOmug%3D%3D (Pubitemid 29067954)
20. D Yang J Qu W Li YH Zhang Y Ren DP Wang YD Wu 2002 Cyclic hexapeptide of d, l-alpha-aminoxy acids as a selective receptor for chloride ion J Am Chem Soc 124 42 12410 12411 10.1021/Ja027073y 12381172 10.1021/ja027073y 1:CAS:528:DC%2BD3sXitVOnuw%3D%3D (Pubitemid 35204556)
21. D Yang YH Zhang NY Zhu 2002 Beta(2, 2)-aminoxy acids: a new building block for turns and helices J Am Chem Soc 124 34 9966 9967 10.1021/Ja026966n 12188642 10.1021/ja026966n 1:CAS:528:DC%2BD38XlvVWqur4%3D (Pubitemid 34919715)
22. D Yang W Li J Qu SW Luo YD Wu 2003 A new strategy to induce gamma-turns: peptides composed of alternating alpha-aminoxy acids and alpha-amino acids J Am Chem Soc 125 43 13018 13019 10.1021/Ja036136p 14570462 10.1021/ja036136p 1:CAS:528:DC%2BD3sXnslagtrg%3D (Pubitemid 37305586)
23. D Yang YH Zhang B Li DW Zhang JCY Chan NY Zhu SW Luo YD Wu 2004 Effect of side chains on turns and helices in peptides of beta(3)-aminoxy acids J Am Chem Soc 126 22 6956 6966 10.1021/Ja049976a 15174865 10.1021/ja049976s 1:CAS:528:DC%2BD2cXjvVSgsro%3D (Pubitemid 38855394)
24. D Yang X Li YF Fan DW Zhang 2005 Enantioselective recognition of carboxylates: a receptor derived from alpha-aminoxy acids functions as a chiral shift reagent for carboxylic acids J Am Chem Soc 127 22 7996 7997 10.1021/Ja051072z 15926807 10.1021/ja051072z 1:CAS:528:DC%2BD2MXjvF2hsb4%3D (Pubitemid 40799637)
25. D Yang X Li Y Sha YD Wu 2005 A cyclic hexapeptide comprising alternating alpha-aminoxy and alpha-amino acids is a selective chloride ion receptor Chem-Eur J 11 10 3005 3009 10.1002/chem.200500098 15761910 10.1002/chem. 200500098 1:CAS:528:DC%2BD2MXksFarsb8%3D (Pubitemid 40672457)