24960-12-1

Basic information

• Product Name: thymidine diphosphate-L-rhamnose
• CAS NO: 24960-12-1
• Molecular Weight: 548.334
• Mol File: 24960-12-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: thymidine diphosphate-L-rhamnose(CAS DataBase Reference)
• NIST Chemistry Reference: thymidine diphosphate-L-rhamnose(24960-12-1)
• EPA Substance Registry System: thymidine diphosphate-L-rhamnose(24960-12-1)

Safety Data

• Hazardous Substances Data: 24960-12-1(Hazardous Substances Data)

Upstream product

• 7132-58-3 dTDP-4-keto-6-deoxy-D-glucose 
• 2196-62-5 thymidine 5'-(α-D-glucopyranosyl diphosphate) 

Downstream Products

• 62012-79-7 TDP-6-deoxy-D-gulose 

Relevant articles and documents

Mechanistic studies of the radical S-adenosylmethionine enzyme DesII with TDP-D-fucose

DesII is a radical S-adenosylmethionine (SAM) enzyme that catalyzes the C4-deamination of TDP-4-amino-4,6-dideoxyglucose through a C3 radical intermediate. However, if the C4 amino group is replaced with a hydroxy group (to give TDP-quinovose), the hydroxy group at C3 is oxidized to a ketone with no C4-dehydration. It is hypothesized that hyperconjugation between the C4 C-N/O bond and the partially filled p orbital at C3 of the radical intermediate modulates the degree to which elimination competes with dehydrogenation. To investigate this hypothesis, the reaction of DesII with the C4-epimer of TDP-quinovose (TDP-fucose) was examined. The reaction primarily results in the formation of TDP-6-deoxygulose and likely regeneration of TDP-fucose. The remainder of the substrate radical partitions roughly equally between C3-dehydrogenation and C4-dehydration. Thus, changing the stereochemistry at C4 permits a more balanced competition between elimination and dehydrogenation.

Studies of deoxyribonucleic acid synthesis and cell growth in the deoxyriboside-requiring bacteria, Lactobacillus acidophilus. III. Identification of thymidine diphosphate rhamnose.

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