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MetaCyc Pathway: dTDP-L-rhamnose biosynthesis II
Traceable author statement to experimental support

Pathway diagram: dTDP-L-rhamnose biosynthesis II

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: BiosynthesisCarbohydrates BiosynthesisSugars BiosynthesisSugar Nucleotides BiosynthesisdTDP-sugar BiosynthesisdTDP-L-Rhamnose-Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col

Expected Taxonomic Range: Magnoliophyta

General Background

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)..

Pathway Characteristics:

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.

Citations: [Reiter01]

Variants: dTDP-L-rhamnose biosynthesis I

Unification Links: AraCyc:PWY-3221


Barber61: Barber GA, Neufeld EF (1961). "Rhamnosyl transfer from TDPL-rhamnose catalyzed by a plant enzyme." Biochem Biophys Res Commun 6;44-8. PMID: 13864832

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

Reiter01: Reiter WD, Vanzin GF (2001). "Molecular genetics of nucleotide sugar interconversion pathways in plants." Plant Mol Biol 47(1-2);95-113. PMID: 11554483

Watt04: Watt G, Leoff C, Harper AD, Bar-Peled M (2004). "A bifunctional 3,5-epimerase/4-keto reductase for nucleotide-rhamnose synthesis in Arabidopsis." Plant Physiol 134(4);1337-46. PMID: 15020741

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

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

Allard04: Allard ST, Cleland WW, Holden HM (2004). "High resolution X-ray structure of dTDP-glucose 4,6-dehydratase from Streptomyces venezuelae." J Biol Chem 279(3);2211-20. PMID: 14570895

Bairoch93: Bairoch A, Boeckmann B (1993). "The SWISS-PROT protein sequence data bank, recent developments." Nucleic Acids Res. 21:3093-3096. PMID: 8332529

Bernstein65: Bernstein R, Robbins P "Control aspects of uridine 5'-diphosphate glucose and thymidine 5'-diphosphate glucose synthesis by microbial enzymes." J Biol Chem 1965;240(1):391-397.

BRENDA14: BRENDA team (2014). Imported from BRENDA version existing on Aug 2014.

Chen09b: 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, MatsuhashiM, 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.

Kaminski14: Kaminski L, Eichler J (2014). "Haloferax volcanii N-glycosylation: delineating the pathway of dTDP-rhamnose biosynthesis." PLoS One 9(5);e97441. PMID: 24831810

Kharel10: Kharel MK, Nybo SE, Shepherd MD, Rohr J (2010). "Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters." Chembiochem 11(4);523-32. PMID: 20140934

Kharel11: Kharel MK, Lian H, Rohr J (2011). "Characterization of the TDP-D-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-D-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate." Org Biomol Chem 9(6);1799-808. PMID: 21264378

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lee04a: 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

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sun May 1, 2016, biocyc13.