A novel strategy for enzymatic synthesis of 4-hydroxyisoleucine: Identification of an enzyme possessing HMKP (4-hydroxy-3-methyl-2-keto- pentanoate) aldolase activity

FEMS Microbiology Letters

Volumn 273, Issue 1, 2007, Pages 70-77

  Smirnov, Sergey V ^a,d   Samsonova, Natalya N ^a   Novikova, Anna E ^a   Matrosov, Nikolay G ^a   Rushkevich, Natalya Y ^a   Kodera, Tomohiro ^b   Ogawa, Jun ^c   Yamanaka, Hiroyuki ^c   Shimizu, Sakayu ^c  

^a Ajinomoto Genetika Research Institute   (Russian Federation)

^b AJINOMOTO CO INC   (Japan)

^c KYOTO UNIVERSITY   (Japan)

^d Ajinomoto Genetika Research Institute   (Russian Federation)

Author keywords

4 hydroxyisoleucine; Biotransformation; HpcH HpaI aldolase family; Type II diabetes

Indexed keywords

4 HYDROXYISOLEUCINE; FRUCTOSE BISPHOSPHATE ALDOLASE;

ALDOL REACTION; AMINATION; AMINO ACID SYNTHESIS; ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME MECHANISM; ENZYME PURIFICATION; ENZYME SYNTHESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL;

ACETALDEHYDE; ARTHROBACTER; BACTERIAL PROTEINS; BASE SEQUENCE; BUTYRIC ACIDS; DNA, BACTERIAL; FRUCTOSE-BISPHOSPHATE ALDOLASE; GLUTAMIC ACID; ISOLEUCINE; MOLECULAR SEQUENCE DATA; SEQUENCE ANALYSIS, DNA; TRANSAMINASES;

PIMELOBACTER SIMPLEX;

EID: 34347407802     PISSN: 03781097     EISSN: 15746968     Source Type: Journal    
DOI: 10.1111/j.1574-6968.2007.00783.x     Document Type: Article

References (19)

1. Alcock NW, Crout DHG, Gregorio MVM, Lee E, Pike G Samuel CJ (1989) Stereochemistry of the 4-hydroxyisoleucine from Trigonella foenum-graecum. Phytochemistry 28 : 1835 1841.
2. Berger BJ, English S, Chan G Knodel MH (2003) Methionine regeneration and aminotransferases in Bacillus subtilis, Bacillus cereus, and Bacillus anthracis. J Bacteriol 185 : 2418 2431.
3. Broca C, Gross R, Petit P, Sauvaire Y, Manteghetti M, Turnier M, Masiello P, Gomis R Ribes G (1999) 4-Hydroxyisoleucine: experimental evidence of its insulinotropic and antidiabetic properties. Am J Physiol Endocrinol Metab 277 : 617 623.
4. Broca C, Breil V, Cruciani-Guglielmacci C et al 2004) Insulinotropic agent ID-1101 (4-hydroxyisoleucine) activates insulin signaling in rat. Am J Physiol Endocrinol Metab 287 : 463 471.
5. Fowden L, Pratt HM Smith A (1973) 4-Hydroxyisoleucine from seed of Trigonella foenum graecum. Phytochemistry 12 : 1707 1711.
6. Hall TR, Wallin R, Reinhart GD Hutson SM (1993) Branched chain aminotransferase isoenzymes. J Biol Chem 268 : 3092 3098.
7. Horswill AR Escalante-Semerena JC (1999) Salmonella typhimurium LT2 catabolizes propionate via the 2-methylcitric acid cycle1. J Bacteriol 181 : 5615 5623.
8. Izard T Blackwell NC (2000) Crystal structures of the metal-dependent 2-dehydro-3-deoxy-galactarate aldolase suggest a novel reaction mechanism. EMBO Journal 19 : 3849 3856.
9. Jackson J Bessler R (1981) Clinical pharmacology of sulfonylurea hypoglycemic agents. Drugs 22 : 211 245.
10. Jennings A, Wilson R Ward R (1989) Symptomatic hypoglycemia in NIDDM patients treated with oral hypoglycemic agents. Diabetes Care 12 : 203 208.
11. Liu WT, Marsh TL, Cheng H Forney LJ (1997) Characterization of microbial diversity by determining terminal restriction fragment length polymorphisms of genes encoding 16S rRNA. Appl Environ Microbiol 63 : 4516 4522.
12. Mamer OA Reimer MLJ (1992) On the mechanisms of the formation of L-alloisoleucine and the 2-hydroxy-3-methylvaleric acid stereoisomers from L-isoleucine in maple syrup urine disease patients and in normal humans. J Biol Chem 267 : 22141 22147.
13. Mushkambarov NN (1996) Analytical Biochemistry, Vol. 3. Forwarder, Moscow.
14. Rolland-Fulcrand V, Rolland M, Roumestant M-L Martinez J (2004) Chemoenzymatic synthesis of enantiomerically pure (2S,3R,4S)-4- hydroxyisoleucine, an insulinotropic amino acid isolated from fenugreek seeds. Eur J Org Chem 2004 : 873 877.
15. Romine MF, Stillwell LC, Wong K-K, Thurston SJ, Sisk EC, Sensen C, Gaasterland T, Fredrickson JK Saffer JD (1999) Complete sequence of a 184-kilobase catabolic plasmid from Sphingomonas aromaticivorans F199. J Bacteriol 181 : 1585 1602.
16. Sauvaire Y, Petit P, Broca C et al 1998) 4-Hydroxyisoleucine: a novel amino acid potentiator of insulin secretion. Diabetes 47 : 206 210.
17. Takahashi Y, Kato K, Hayashizaki Y, Wakabayashi T, Ohtsuka E, Matsuki S, Ikehara M Matsubara K (1985) Molecular cloning of the human cholecystokinin gene by use of a synthetic probe containing deoxyinosine. Proc Natl Acad Sci USA 82 : 1931 1935.
18. Wang Q, Ouazzani J, Sasaki NA Potier P (2002) A practical synthesis of (2S,3R,4S)-4-hydroxyisoleucine, a potent insulinotropic a-amino acid from fenugreek. Eur J Org Chem 834 839.
19. Wright A, Blewett A, Fulop V, Cooper R, Burrows S, Jones C Roper D (2002) Expression, purification, crystallization and preliminary characterization of an HHED aldolase homologue from Escherichia coli K12. Acta Crystallogr D Biol Crystallogr 58 : 2191 2193.