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1.1.1.133

Accepted name:

dTDP-4-dehydrorhamnose reductase

Reaction:

dTDP-β-L-rhamnose + NADP⁺ = dTDP-4-dehydro-β-L-rhamnose + NADPH + H⁺

For diagram of dtdp-6-deoxyhexose biosynthesis, click here and for diagram of 6-deoxyhexose biosynthesis, click here

Glossary:

dTDP-4-dehydro-β-L-rhamnose = dTDP-4-dehydro-6-deoxy-β-L-mannose
dTDP-4-β-L-rhamnose = dTDP-6-deoxy-β-L-mannose

Other name(s):

dTDP-4-keto-L-rhamnose reductase; dTDP-4-ketorhamnose reductase; TDP-4-keto-rhamnose reductase; thymidine diphospho-4-ketorhamnose reductase; dTDP-6-deoxy-L-mannose:NADP⁺ 4-oxidoreductase; dTDP-6-deoxy-β-L-mannose:NADP⁺ 4-oxidoreductase

Systematic name:

dTDP-β-L-rhamnose:NADP⁺ 4-oxidoreductase

Comments:

In the reverse direction, reduction on the 4-position of the hexose moiety takes place only while the substrate is bound to another enzyme that catalyses epimerization at C-3 and C-5; the complex has been referred to as dTDP-L-rhamnose synthase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 37250-64-9

References:

1.	Melo, A. and Glaser, L. The mechanism of 6-deoxyhexose synthesis. II. Conversion of deoxythymidine diphosphate 4-keto-6-deoxy-D-glucose to deoxythymidine diphosphate L-rhamnose. J. Biol. Chem. 243 (1968) 1475–1478. [PMID: 4384782]

[EC 1.1.1.133 created 1972]

2.4.1.289

Accepted name:

N-acetylglucosaminyl-diphospho-decaprenol L-rhamnosyltransferase

Reaction:

dTDP-6-deoxy-β-L-mannose + N-acetyl-α-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + α-L-rhamnopyranosyl-(1→3)-N-acetyl-α-D-glucosaminyl-diphospho-trans,octacis-decaprenol

For diagram of galactofuranan biosynthesis, click here

Glossary:

dTDP-6-deoxy-β-L-mannose = dTDP-4-β-L-rhamnose

Other name(s):

WbbL

Systematic name:

dTDP-6-deoxy-β-L-mannose:N-acetyl-α-D-glucosaminyl-diphospho-trans,octacis-decaprenol 3-α-L-rhamnosyltransferase

Comments:

Requires Mn²⁺ or Mg²⁺. Isolated from Mycobacterium smegmatis [1] and Mycobacterium tuberculosis [2]. The enzyme catalyses the addition of a rhamnosyl unit to N-acetyl-α-D-glucosaminyl-diphospho-trans,octacis-decaprenol, completing the synthesis of the linkage unit that attaches the arabinogalactan moiety to the peptidoglycan moiety in Mycobacterial cell wall.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Mills, J.A., Motichka, K., Jucker, M., Wu, H.P., Uhlik, B.C., Stern, R.J., Scherman, M.S., Vissa, V.D., Pan, F., Kundu, M., Ma, Y.F. and McNeil, M. Inactivation of the mycobacterial rhamnosyltransferase, which is needed for the formation of the arabinogalactan-peptidoglycan linker, leads to irreversible loss of viability. J. Biol. Chem. 279 (2004) 43540–43546. [DOI] [PMID: 15294902]
2.	Grzegorzewicz, A.E., Ma, Y., Jones, V., Crick, D., Liav, A. and McNeil, M.R. Development of a microtitre plate-based assay for lipid-linked glycosyltransferase products using the mycobacterial cell wall rhamnosyltransferase WbbL. Microbiology 154 (2008) 3724–3730. [DOI] [PMID: 19047740]

[EC 2.4.1.289 created 2012]

2.4.1.331

Accepted name:

8-demethyltetracenomycin C L-rhamnosyltransferase

Reaction:

dTDP-β-L-rhamnose + 8-demethyltetracenomycin C = dTDP + 8-demethyl-8-α-L-rhamnosyltetracenomycin C

For diagram of elloramycin biosynthesis, click here

Glossary:

dTDP-β-L-rhamnose = dTDP-6-deoxy-β-L-mannose

Other name(s):

elmGT

Systematic name:

dTDP-β-L-rhamnose:8-demethyltetracenomycin C 3-α-L-rhamnosyltransferase

Comments:

Isolated from Streptomyces olivaceus Tü2353. Involved in elloramycin biosynthesis. In vitro it can also utilize other 6-deoxy D- or L-hexoses.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Blanco, G., Patallo, E.P., Brana, A.F., Trefzer, A., Bechthold, A., Rohr, J., Mendez, C. and Salas, J.A. Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin. Chem. Biol. 8 (2001) 253–263. [DOI] [PMID: 11306350]

[EC 2.4.1.331 created 2014]

5.1.3.25

Accepted name:

dTDP-L-rhamnose 4-epimerase

Reaction:

dTDP-6-deoxy-β-L-talose = dTDP-β-L-rhamnose

Glossary:

dTDP-β-L-rhamnose = dTDP-6-deoxy-β-L-mannose
dTDP-6-deoxy-β-L-talose = dTDP-β-L-pneumose

Other name(s):

dTDP-4-L-rhamnose 4-epimerase; wbiB (gene name)

Systematic name:

dTDP-6-deoxy-β-L-talose 4-epimerase

Comments:

The equilibrium is strongly towards dTDP-β-L-rhamnose.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Yoo, H.G., Kwon, S.Y., Karki, S. and Kwon, H.J. A new route to dTDP-6-deoxy-L-talose and dTDP-L-rhamnose: dTDP-L-rhamnose 4-epimerase in Burkholderia thailandensis. Bioorg. Med. Chem. Lett. 21 (2011) 3914–3917. [DOI] [PMID: 21640586]

[EC 5.1.3.25 created 2012]