This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.
|Superclasses:||Biosynthesis → Carbohydrates Biosynthesis → Sugars Biosynthesis → Sugar Nucleotides Biosynthesis → dTDP-sugar Biosynthesis → dTDP-L-Rhamnose-Biosynthesis|
Some taxa known to possess this pathway include : Arabidopsis thaliana col
Expected Taxonomic Range: Magnoliophyta
L-Rhamnose is a component of the plant cell wall pectic polysaccharides rhamnogalacturonan I and rhamnogalacturonan II and is also present in diverse secondary metabolites including anthocyanins, flavonoids and triterpenoids. Rhamnosyl transferases have been shown to utilize UDP-β-L-rhamnose as the donor substrate [BarPeled91, Watt04], although in mung bean (Vigna radiata), both dTDP-β-L-Rhamnose and UDP-β-L-rhamnose were reported to act as sugar donors for the rhamnosylation of flavonoids [Barber61]. In general UDP-D-glucose is used in plants rather than dTDP-D-glucose as a precursor in the de novo synthesis of nucleotide-L-rhamnose (NDP-L-rhamnose) (see pathway UDP-L-rhamnose biosynthesis)..
Compared to the bacterial biosynthesis pathway for dTDP-L-rhamnose (see dTDP-L-rhamnose biosynthesis I), its plant homologue is shorter. The last two enzymatic activities (epimerase and reductase) are performed in plants by one unique enzyme, NRS/ER [Watt04]. To date the existence of a dTDP-D-glucose-4,6-dehydratase has not been experimentally proven in plants.
Variants: dTDP-L-rhamnose biosynthesis I
Unification Links: AraCyc:PWY-3221
BarPeled91: Bar-Peled M, Lewinsohn E, Fluhr R, Gressel J (1991). "UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus." J Biol Chem 266(31);20953-9. PMID: 1939145
Aguirrezabalaga00: Aguirrezabalaga I, Olano C, Allende N, Rodriguez L, Brana AF, Mendez C, Salas JA (2000). "Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus." Antimicrob Agents Chemother 44(5);1266-75. PMID: 10770761
Chen09a: Chen YL, Chen YH, Lin YC, Tsai KC, Chiu HT (2009). "Functional characterization and substrate specificity of spinosyn rhamnosyltransferase by in vitro reconstitution of spinosyn biosynthetic enzymes." J Biol Chem 284(11);7352-63. PMID: 19126547
GILBERT65: GILBERT JM, MATSUHASHI M, STROMINGER JL (1965). "THYMIDINE DIPHOSPHATE 4-ACETAMIDO-4,6-DIDEOXYHEXOSES. II. PURIFICATION AND PROPERTIES OF THYMIDINE DIPHOSPHATE D-GLUCOSE OXIDOREDUCTASE." J Biol Chem 240;1305-8. PMID: 14284740
Gross00: Gross JW, Hegeman AD, Vestling MM, Frey PA (2000). "Characterization of enzymatic processes by rapid mix-quench mass spectrometry: the case of dTDP-glucose 4,6-dehydratase." Biochemistry 39(45);13633-40. PMID: 11076501
Hegeman01: Hegeman AD, Gross JW, Frey PA (2001). "Probing catalysis by Escherichia coli dTDP-glucose-4,6-dehydratase: identification and preliminary characterization of functional amino acid residues at the active site." Biochemistry 40(22);6598-610. PMID: 11380254
Heichan04: Heichan, L., Sohng, J., Kim, H., Nam, D., Seong, C., Han, J., Yoo, J. (2004). "Cloning, Expression, and Biochemical Characterization of dTDP-Glucose 4,6-Dehydratase Gene (gerE) from Streptomyces sp. GERI-155." Journal of microbiology and biotechnology 14(3):576-583.
Lee04: Lee HC, Sohng JK, Kim HJ, Nam DH, Han JM, Cho SS, Choi JH, Yoo JC (2004). "Cloning and expression of the glucose-1-phosphate thymidylyltransferase gene (gerD) from Streptomyces sp. GERI-155." Mol Cells 17(2);274-80. PMID: 15179042
Lombo97: Lombo F, Siems K, Brana AF, Mendez C, Bindseil K, Salas JA (1997). "Cloning and insertional inactivation of Streptomyces argillaceus genes involved in the earliest steps of biosynthesis of the sugar moieties of the antitumor polyketide mithramycin." J Bacteriol 179(10);3354-7. PMID: 9150235
Madduri01: Madduri K, Waldron C, Merlo DJ (2001). "Rhamnose biosynthesis pathway supplies precursors for primary and secondary metabolism in Saccharopolyspora spinosa." J Bacteriol 183(19);5632-8. PMID: 11544225
Marolda95: Marolda CL, Valvano MA (1995). "Genetic analysis of the dTDP-rhamnose biosynthesis region of the Escherichia coli VW187 (O7:K1) rfb gene cluster: identification of functional homologs of rfbB and rfbA in the rff cluster and correct location of the rffE gene." J Bacteriol 1995;177(19);5539-46. PMID: 7559340
Melo68: Melo A, Elliott WH, Glaser L (1968). "The mechanism of 6-deoxyhexose synthesis. I. Intramolecular hydrogen transfer catalyzed by deoxythymidine diphosphate D-glucose oxidoreductase." J Biol Chem 1968;243(7);1467-74. PMID: 4869560
MersonDavies94: Merson-Davies LA, Cundliffe E (1994). "Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome." Mol Microbiol 13(2);349-55. PMID: 7984112
Naundorf96: Naundorf A, Klaffke W (1996). "Substrate specificity of native dTDP-D-glucose-4,6-dehydratase: chemo-enzymatic syntheses of artificial and naturally occurring deoxy sugars." Carbohydr Res 285;141-50. PMID: 9011374
Oliynyk07: Oliynyk M, Samborskyy M, Lester JB, Mironenko T, Scott N, Dickens S, Haydock SF, Leadlay PF (2007). "Complete genome sequence of the erythromycin-producing bacterium Saccharopolyspora erythraea NRRL23338." Nat Biotechnol 25(4);447-53. PMID: 17369815
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