Synthesis of functional dipeptide carnosine from nonprotected amino acids using carnosinase-displaying yeast cells

Applied Microbiology and Biotechnology

Volumn 86, Issue 6, 2010, Pages 1895-1902

  Inaba, Chiaki ^a   Higuchi, Shinsuke ^a   Morisaka, Hironobu ^a   Kuroda, Kouichi ^a   Ueda, Mitsuyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Carnosinase (CN1); Carnosine; Cell surface display; Cell surface engineering; Functional dipeptide; Whole cell biocatalyst

Indexed keywords

CARNOSINE; CELL SURFACE DISPLAYS; CELL SURFACE ENGINEERING; DIPEPTIDE; WHOLE CELL BIOCATALYSTS;

AMINO ACIDS; CELL MEMBRANES; HYDROPHOBICITY; IONIC LIQUIDS; IONIZATION OF LIQUIDS; ORGANIC ACIDS; ORGANIC SOLVENTS; PHOSPHATASES; SURFACES; SYNTHESIS (CHEMICAL); WATER CONTENT; YEAST;

CYTOLOGY;

AGGLUTININ; AMINO ACID; CARNOSINE; DIPEPTIDE CARNOSINE; HYDROLASE; IONIC LIQUID; ORGANIC SOLVENT; UNCLASSIFIED DRUG;

AMINO ACID; ANTIOXIDANT; BIOACTIVITY; BIOENGINEERING; CATALYST; CYTOPLASM; CYTOPLASMIC INCOMPATIBILITY; ENZYME ACTIVITY; GENE; HYDROPHOBICITY; PEPTIDE; PROTEIN; SOLVENT; SUBSTRATE; WATER CONTENT; YEAST;

ARTICLE; CATALYSIS; CELL SURFACE; FREEZE DRYING; HYDROPHOBICITY; IMMUNOFLUORESCENCE; MOLECULAR CLONING; NONHUMAN; PROTEIN SYNTHESIS; YEAST CELL;

BETA-ALANINE; BIOCATALYSIS; CARNOSINE; CLONING, MOLECULAR; DIPEPTIDASES; FREEZE DRYING; HISTIDINE; HUMANS; HYDROLYSIS; HYDROPHOBICITY; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE; SOLVENTS; SUBSTRATE SPECIFICITY; TRANSFORMATION, GENETIC;

EID: 77952881447     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2396-7     Document Type: Article

References (25)

1. H Abe 2000 Role of histidine-related compounds as intracellular proton buffering constituents in vertebrate muscle Biochemistry (Mosc) 65 757 765 1:CAS:528:DC%2BD3cXlvFOlsb4%3D
2. EJ Baran 2000 Metal complexes of carnosine Biochemistry (Mosc) 65 789 797 1:CAS:528:DC%2BD3cXlvFOlsbs%3D
3. B Eker P Asuri S Murugesan RJ Linhardt JS Dordick 2007 Enzyme-carbon nanotube conjugates in room-temperature ionic liquids Appl Biochem Biotechnol 143 153 163 10.1007/s12010-007-0035-2 1:CAS:528:DC%2BD2sXhtlSktLvN (Pubitemid 350242519)
4. T Heck HP Kohler M Limbach O Flögel D Seebach B Geueke 2007 Enzyme-catalyzed formation of β-peptides: β-peptidyl aminopeptidases BapA and DmpA acting as β-peptide-synthesizing enzymes Chem Biodivers 4 2016 2030 10.1002/cbdv.200790168 1:CAS:528:DC%2BD2sXhtFelsrzE (Pubitemid 47527662)
5. AR Hipkiss 1998 Glycation, ageing and carnosine: are carnivorous diets beneficial? Int J Biochem Cell Biol 30 863 868 10.1016/S1357-2725(98)00060-0 1:CAS:528:DyaK1cXls1Ohtbw%3D (Pubitemid 28383391)
6. TP Hopp KS Prickett VL Price RT Libby CJ March DP Cerretti DL Urdal PJ Conlon 1988 A short polypeptide marker sequence useful for recombinant protein identification and purification Biotechnology 6 1204 1210 10.1038/nbt1088-1204 1:CAS:528:DyaL1MXptFKjuw%3D%3D
7. H Horinishi M Grillo FL Margolis 1978 Purification and characterization of carnosine synthetase from mouse olfactory bulbs J Neurochem 31 909 919 10.1111/j.1471-4159.1978.tb00127.x 1:CAS:528:DyaE1MXhsVOntbs%3D
8. AM Klibanov 2001 Improving enzymes by using them in organic solvents Nature 409 241 246 10.1038/35051719 1:CAS:528:DC%2BD3MXlvFWiuw%3D%3D (Pubitemid 32144293)
9. K Kuroda K Matsui S Higuchi A Kotaka H Sahara Y Hata M Ueda 2009 Enhancement of display efficiency in yeast display system by vector engineering and gene disruption Appl Microbiol Biotechnol 82 713 719 10.1007/s00253-008- 1808-4 1:CAS:528:DC%2BD1MXisVWkur4%3D
10. C Laane S Boeren K Vos C Veeger 1987 Rules for optimization of biocatalysis in organic solvents Biotechnol Bioeng 30 81 87 10.1002/bit. 260300112 1:CAS:528:DyaL2sXltFChsbg%3D
11. SJ Li Y Zhao YB Huang G Gao DH Zhang L Xu G Li XZ Zhang 2008 Synthesis of a precursor dipeptide of thymopentin in organic solvents by an enzymatic method Prep Biochem Biotechnol 38 158 171 10.1080/10826060701884665 (Pubitemid 351341791)
12. AF Mannion PM Lakeman M Dunnett RC Harris PL Willan 1992 Carnosine and anserine concentrations in the quadriceps femoris muscle of healthy humans Eur J Appl Physiol 64 47 50 10.1007/BF00376439 1:STN:280:DyaK387jslajtw%3D%3D
13. GA McFarland R Holliday 1994 Retardation of the senescence of cultured human diploid fibroblasts by carnosine Exp Cell Res 167 175 184
14. NM Micaêlo CM Soares 2007 Modeling hydration mechanisms of enzymes in nonpolar and polar organic solvents FEBS J 274 2424 2436 10.1111/j.1742-4658. 2007.05781.x (Pubitemid 46633469)
15. K Nakashima T Maruyama N Kamiya M Goto 2005 Comb-shaped poly(ethylene glycol)-modified subtilisin Carlsberg is soluble and highly active in ionic liquids Chem Commun (Camb) 34 4297 4299 10.1039/b505479f (Pubitemid 41345341)
16. P Quinn A Boldyrev V Formazuyk 1992 Carnosine: its properties, functions and potential therapeutic applications Mol Aspects Med 13 379 444 10.1016/0098-2997(92)90006-L 1:CAS:528:DyaK3sXksVSju70%3D (Pubitemid 23152963)
17. F Sanger S Nicklen AR Coulson 1977 DNA sequencing with chain-terminating inhibitors Proc Natl Acad Sci USA 74 5463 5467 10.1073/pnas.74.12.5463 1:CAS:528:DyaE1cXhtlaru7Y%3D
18. H Sekizaki K Itoh A Shibuya E Toyota M Kojoma K Tanizawa 2008 Trypsin-catalyzed synthesis of dipeptide containing α-aminoisobutylic acid using p- and m-(Amidinomethyl)phenyl esters as acyl donor Chem Pharm Bull 56 688 691 10.1248/cpb.56.688 1:CAS:528:DC%2BD1cXot1Ortbg%3D (Pubitemid 351669438)
19. W Soetaert E Vandamme 2006 The impact of industrial biotechnology Biotechnol J 1 756 769 10.1002/biot.200600066 1:CAS:528:DC%2BD28XhtFSqurvJ
20. U Stottmeister A Aurich H Wilde J Andersch S Schmidt D Sicker 2005 White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical synthesis J Ind Microbiol Biotech 32 651 664 10.1007/s10295-005-0254-x 1:CAS:528:DC%2BD2MXht1Oks7rJ (Pubitemid 41752149)
21. R Tabakman P Lazarovici R Kohen 2002 Neuroprotective effects of carnosine and homocarnosine on pheochromocytoma PC12 cells exposed to ischemia J Neurosci Res 68 463 469 10.1002/jnr.10228 1:CAS:528:DC%2BD38XjsFGqs7w%3D (Pubitemid 34461577)
22. M Teufel V Saudek JP Ledig A Bernhardt S Boularand A Carreau NJ Cairns C Carter DJ Cowley D Duverger AJ Ganzhorn C Guenet B Heintzelmann V Laucher C Sauvage T Smirnova 2003 Sequence identification and characterization of human carnosinase and a closely related non-specific dipeptidase J Biol Chem 278 6521 6531 10.1074/jbc.M209764200 1:CAS:528:DC%2BD3sXht1ejsLY%3D (Pubitemid 36800914)
23. PQ Trombley MS Horning LJ Blakemore 2000 Interactions between carnosine and zinc and copper: implications for neuromodulation and neuroprotection Biochemistry (Mosc) 65 807 816 1:CAS:528:DC%2BD3cXlvFOlsbk%3D
24. S Voss A Skerra 1997 Mutagenesis of a flexible loop in streptavidin leads to higher affinity for the Strep-tag II peptide and improved performance in recombinant protein purification Protein Eng 10 975 982 10.1093/protein/10.8.975 1:CAS:528:DyaK2sXnsl2kt7g%3D
25. T Welton 1999 Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem Rev 99 2071 2084 10.1021/cr980032t 1:CAS:528:DyaK1MXkt1artrw%3D