Enzymatic synthesis and characterization of L-methionine and 2-hydroxy-4-(methylthio)butanoic acid (HMB) co-oligomers

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 9, 2003, Pages 2461-2467

  Rajesh, Mathur ^a   Kapila, Shubhen ^a   Nam, Paul ^a   Forciniti, Daniel ^a   Lorbert, Stephen ^b   Schasteen, Charles ^b  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

^b NOVUS INTERNATIONAL INC   (United States)

Author keywords

Co oligomers; HMB; Mass spectrometry; Methionine; Methionine hydroxy analogue; MHA; Oligopeptides; Papain

Indexed keywords

2 HYDROXY 4 (METHYLTHIO)BUTANOIC ACID; BUTYRIC ACID DERIVATIVE; METHIONINE; OLIGOMER; PAPAIN; UNCLASSIFIED DRUG;

ARTICLE; ENZYME MECHANISM; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; REVERSED PHASE LIQUID CHROMATOGRAPHY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MASS SPECTROMETRY; METHIONINE; PAPAIN;

EID: 0037462037     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf026093g     Document Type: Article

References (25)

1. Chalupa, W. Rumen bypass and protection of proteins and amino acids. J. Dairy Sci. 1975, 58, 1198-1218.
2. Schwab, G. C.; Satter, L. D.; Clay, A. B. Response of lactating dairy cows to abomasal infusion of amino acids. J. Dairy Sci. 1976, 59, 1254-1269.
3. Schwab, G. C.; Bozak, C. K.; Whitehouse, N. L.; Mesbah, M. M. A. Amino acid limitation and flow to duodenum at four stages of lactation. I. Sequence of lysine and methionine limitation. J. Dairy Sci. 1992, 75, 3486-3502.
4. Dibner J. J.; Knight, C. D. Conversion of 2-hydroxy-4-(methylthio)butanoic acid to L-methionine in the chick: A stereospecific pathway. J. Nutr. 1984, 114, 1716-1723.
5. Dibner, J. J. Utilization of supplementation methionine sources by primary cultures of chick hepatocytes. J. Nutr. 1983, 113, 2116-2123.
6. Patterson, J. A.; Kung, L., Jr. Metabolism of DL-methionine and methionine analogues by rumen microorganisms. J. Dairy Sci. 1988, 71, 3292-3301.
7. Belasco, I. J. Fate of carbond-14 labeled methionine hydroxy analogue and methionine in the lactating dairy cows. J. Dairy Sci. 1980, 63, 775-784.
8. Koenig, K. M.; Rode, L. M.; Knight C. D.; McCullough, P. R. Ruminal escape, gastrointestinal absorption, and response of serum methionine to supplementation of liquid methionine hydroxy analogue in dairy cows. J. Dairy Sci. 1999, 82, 355-361.
9. Pas Bernard, J. K. Supplemental animal-marine protein blend and a rumen protected methionine hydroxy analogue for lactating dairy cows. Prof. Anim. Sci. 1997, 13, 149-154.
10. Ferjancic, A.; Puigserver, A.; Gaertner, H. Papain-catalyzed polymerization of amino acids in low water organic solvents. Biotechnol. Lett. 1991, 13, 161-166.
11. Brenner, M.; Muller, H. R.; Pfister, R. W. A new enzymic peptide synthesis. I. Helv. Chim. Acta 1950, 33, 568-591.
12. Brenner, M.; Pfister, R. W. Enzymic peptide synthesis. II. Isolation of enzymatically manufactured L-methionyl-L-methionine and L-methionyl-L-methionyl-L-methionine; A comparison with synthetic products. Helv. Chim. Acta 1951, 34, 2085-2096.
13. Dannenberg, A. M.; Smith, E. L. Action of proteinase I of bovine lung. Hydrolysis of the oxidized B chain of insulin; Polymer formation from amino acid esters. J. Biol. Chem. 1955, 215, 55-67.
14. Anderson, G.; Luisi, P. L. Papain-induced oligomerization of α-amino acid esters. Helv. Chim. Acta 1979, 62, 488-494.
15. Sluyterman, L. Æ.; Wijdenes, J. Sigmoidal progress curves in the polymerization of leucine methyl ester catalyzed by papain. Biochim. Biophys. Acta 1972, 289, 194-202.
16. Selvi, C.; Baboulene, M.; Speziale, V.; Lattes, A. Synthesis by enzymic catalysis II. Amino acid polymerization. J. Chem. Technol. Biotechnol. 1985, 35B, 282-290.
17. Aso, K.; Uemura, T.; Shiokawa, Y. Protease-catalyzed synthesis of oligo-L-glutamic acid from L-glutamic acid diethyl ester. Agric. Biol. Chem. 1988, 52, 2443-2449.
18. Arai, S.; Yamashita, M.; Fujimaki, M. A novel one-step process for enzymatic incorporation of amino acids into proteins: Papain-catalyzed polymerization of L-methionine ethyl ester and its regulation by adding a protein substrate. Agric. Biol. Chem. 1979, 43, 1069-1079.
19. Jost, R.; Brambilla, E.; Monti, J. C.; Luisi, P. L. Papain catalyzed oligomerization of α-amino acids. Synthesis and characterization of water-insoluble oligomers of L-methionine. Helv. Chim. Acta 1980, 63, 375-384.
20. Lee, H.; Fukushi, H.; Uchino, M.; Fukuzawa, Y. Papain catalyzed polymerization of L-α-amino acid methyl esters with hydrophobic side chains. Chem. Express 1990, 5, 741-744.
21. Murgasova, R.; Hercules, D. M. Polymer characterization by combining liquid chromatography with MALDI and ESI mass spectrometry. Anal. Bioanal. Chem. 2002, 373, 481-489.
22. Loo, J. A.; Loo, R. R. O. Electrospray Ionization Mass Spectrometry of Peptides and Proteins. In Electrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation, and Applications; Cole, R. B., Ed.; John Wiley and Sons: New York, 1997; pp 385-419.
23. Dass, C. Principles and Practice of Biological Mass Spectrometry; John Wiley and Sons: New York, 2000.
24. Spindler, M.; Stadler, R.; Tanner, H. Amino acid analysis of feedstuffs: Determination of methionine and cystine after oxidation with performic acid and hydrolysis. J. Agric. Food Chem. 1984, 32, 1366-1371.
25. Kasai, T.; Tanaka, T.; Kiriyama, S. Correlation between molecular weight distribution of oligo-L-methionine prepared by papain-catalyzed polymerization and its supplementary effect in a low protein diet. Biosci., Biotechnol., Biochem. 1992, 56, 1884-1885.