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thymidine diphosphate wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 structure and properties 2 biosynthesis and metabolism toggle biosynthesis and metabolism subsection 2 1 intermediate in dttp synthesis 3 role in thymidine nucleotide homeostasis and telomere biology 4 role in bacterial sugar nucleotide biosynthesis 5 structural biology and enzyme interactions 6 pharmacological and biomedical relevance 7 see also 8 references toggle the table of contents thymidine diphosphate 13 languages تۆرکجه català dansk فارسی français 日本語 한국어 nederlands srpskohrvatski српскохрватски slovenčina српски srpski اردو 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia thymidine diphosphate names iupac name thymidine 5 trihydrogen diphosphate systematic iupac name 2 r 3 s 5 r 3 hydroxy 5 5 methyl 2 4 dioxo 3 4 dihydropyrimidin 1 2 h yl oxolan 2 yl methyl trihydrogen diphosphate identifiers cas number 491 97 4 y 3d model jsmol interactive image chebi chebi 18075 n chemspider 144320 pubchem cid 164628 unii qq3k1p45df y comptox dashboard epa dtxsid801027011 inchi inchi 1s c10h16n2o11p2 c1 5 3 12 10 15 11 9 5 14 8 2 6 13 7 22 8 4 21 25 19 20 23 24 16 17 18 h3 6 8 13h 2 4h2 1h3 h 19 20 h 11 14 15 h2 16 17 18 t6 7 8 m0 s1 key ujlxyodchaelly xlpzgreqsa n smiles cc1 cn c o nc1 o c h 2c c h c h o2 cop o o op o o o o properties chemical formula c 10 h 16 n 2 o 11 p 2 molar mass 402 19 except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa n verify what is y n infobox references chemical compound thymidine diphosphate tdp or deoxythymidine diphosphate dtdp also thymidine pyrophosphate dtpp is a nucleotide diphosphate it is an ester of pyrophosphoric acid with the nucleoside thymidine dtdp consists of the pyrophosphate group the pentose sugar ribose and the nucleobase thymine unlike the other deoxyribonucleotides thymidine diphosphate does not always contain the deoxy prefix in its name 1 structure and properties edit thymidine diphosphate contains a β d 2 deoxyribofuranose ring linked to a thymine pyrimidine base via a β n1 glycosidic bond including a diphosphate chain attached to the 5 position of the sugar in aqueous solution the pyrophosphate group is extensively ionized at physiological ph and is capable of coordinating with divalent metal ions such as mg 2 which is necessary for many nucleotide processing enzymes through analysis of crystal structures of enzymes bound to tdp or to the antiviral analogue azido thymidine phosphate show that a conserved set of lysine histidine and arginine residues allows for the nucleotide to be correctly positioned in the active site 2 biosynthesis and metabolism edit intermediate in dttp synthesis edit in most organisms thymidine diphosphate is a following intermediate in forming thymidine triphosphate dttp a substrate precursor for dna synthesis early research conducted on tumor extracts concluded that atp dependent kinases were responsible for the phosphorylation of thymidine monophosphate dtmp first to thymidine diphosphate then to dttp dtdp was observed to have low accumulation due to its rapid conversion to dttp establishing the diphosphate variant to be an immediate precursor to dttp in mammalian cells 2 thymidine diphosphate is also found within the salvage pathway where thymidine is phosphorylated by thymidine kinase to dtmp which is then further phosphorylated by nucleotide diphosphate kinases analysis of thymidine kinases have used bisubstrate analogues containing tdp to induce conformational changes associated with phosphate transfer 3 role in thymidine nucleotide homeostasis and telomere biology edit a balanced pool of thymidine mono di and triphosphates are crucial for accurate dna replication and repair thymidine nucleotide is found to be involved in various metabolic pathways through use of genome wide functional screening of human cells enzymes such as thymidine kinase 1 tk1 thymidylate synthase tyms and triphosphohydrolase samhd1 help to regulate telomere length and are regulated by tdp disturbances that reduce dtdp and dttp production results in telomere shortening whereas the loss of samhd1 leads to telomere elongation thymidine supplementation or manipulating enzymes that regulate dtdp dttp levels can restore telomere length in cases of telomere biology disorders highlighting the importance of thymidine nucleotide metabolism in human telomere regulation 4 role in bacterial sugar nucleotide biosynthesis edit in widespread species of bacteria thymidine diphosphate is a component of a larger activated sugar donor such as dtdp rhammose dtdp rhammose in particular is generated via glucose 1 phosphate utilizing dttp throughout a conserved four enzyme pathway these four enzymes include rmla d rmla glucose 1 phosphate thymidyltransferase forms dtdp d glucose which then gets converted into a dtdp 6 deoxy d xylo 4 hexulose intermediate via rmlb 4 6 dehydratase this intermediate then gets converted to dtdp l rhammose via rmlc 3 5 epimerase and rmld 4 reductase enzymes 5 dtdp l rhammose is a crucial precursor to polysaccharide structures containing rhammose seen in cell walls and surface structures in various gram positive and gram negative pathogens such as streptococci and mycobacterium tuberculosis disruption in rml enzyme regulation impacts cell wall integrity and virulence highlighting the importance of dtdp linked sugars in bacterial physiology 5 structural biology and enzyme interactions edit thymidine diphosphate is a commonly used substrate in experiments studying nucleotide processing enzymes obtained crystal structures of nucleoside diphosphate kinase ndpk with tdp or azido thymine diphosphate reveal how the nucleotide binds to the active site and how the diphosphate group is transferred to other nucleoside diphosphates utilizing azido thymidine diphosphate revealed the 3 azido substituent displaces a catalytically crucial lysine and disrupts hydrogen bonding between the b and y phosphate group s oxygen explaining how the proviral drug azt is a poor substrate to convert into its triphosphate form via ndpk these studies have provided understanding how kinases recognize thymidine versus thymidylate variants and how mono di and triphosphate forms are all distinguished from one another 6 pharmacological and biomedical relevance edit due to thymidine phosphates relevance in the salvage pathway nucleotide synthesis and metabolic sugar nucleotide pathways enzymes that produce or consume tdp are considered potential drug targets in human cells alteration of thymidine nucleotide metabolism can influence telomere elongation suggesting that the possibility of exploiting pathways involving dtdp and dttp could be useful in treating telomere biology disorders and cancer where telomere length is unregulated 4 in bacteria the dtdp l rhammose pathway is essential for viability in several pathogens assays conducted that monitor the conversion from dtdp glucose to dtdp l rhammose via nadph consumption have been used to identify possible inhibitors to rml enzymes some of these compounds have been shown to inhibit m tuberculosis from widespread growth in culture showcasing the feasibility of targeting tdp sugar biosynthesis for antibiotic development azido thymidine diphosphate s weak ability to convert into its triphosphate form have also provided input in designing nucleoside analogues with improved activation profiles 5 see also edit nucleoside nucleotide dna rna oligonucleotide dtdp glucose references edit coghill anne m garson lorrin r eds 2006 the acs style guide effective communication of scientific diphosphates information 3rd ed washington d c american chemical society p 244 isbn 978 0 8412 3999 9 1 2 ives d h february 1965 evidence for thymidine diphosphate as the precursor of thymidine triphosphate in tumor transfer of the terminal phosphate of adenosine triphosphate to thymidylate the journal of biological chemistry 240 819 824 issn 0021 9258 pmid 14275141 gardberg anna shuvalova ludmilla monnerjahn christian konrad manfred lavie arnon 2003 10 01 structural basis for the dual thymidine and thymidylate kinase activity of herpes thymidine kinases structure 11 10 1265 1277 doi 10 1016 j str 2003 09 003 hdl 11858 00 001m 0000 0012 f016 5 issn 0969 2126 1 2 mannherz william agarwal suneet april 2023 thymidine nucleotide metabolism controls human telomere length nature genetics 55 4 568 580 doi 10 1038 s41588 023 01339 5 issn 1546 1718 1 2 3 ma y stern r j scherman m s vissa v d yan w jones v c zhang f franzblau s g lewis w h mcneil m r may 2001 drug targeting mycobacterium tuberculosis cell wall synthesis genetics of dtdp rhamnose synthetic enzymes and development of a microtiter plate based screen for inhibitors of conversion of dtdp glucose to dtdp rhamnose antimicrobial agents and chemotherapy 45 5 1407 1416 doi 10 1128 aac 45 5 1407 1416 2001 issn 0066 4804 pmc 90481 pmid 11302803 xu yingwu sellam olivier moréra solange sarfati simon biondi ricardo véron michel janin joël 1997 07 08 x ray analysis of azido thymidine diphosphate binding to nucleoside diphosphate kinase proceedings of the national academy of sciences 94 14 7162 7165 doi 10 1073 pnas 94 14 7162 pmc 23778 v t e nucleic acid constituents nucleobase purine adenine guanine hypoxanthine xanthine purine analogue pyrimidine uracil thymine cytosine pyrimidine analogue unnatural base pair ubp nucleoside ribonucleoside adenosine guanosine 5 methyluridine uridine 5 methylcytidine cytidine pseudouridine inosine n 6 methyladenosine xanthosine wybutosine deoxyribonucleoside deoxyadenosine deoxyguanosine thymidine deoxyuridine deoxycytidine deoxyinosine deoxyxanthosine nucleotide nucleoside monophosphate ribonucleotide amp gmp m 5 ump ump cmp imp xmp deoxyribonucleotide damp dgmp dtmp dump dcmp dimp dxmp cyclic nucleotide camp cgmp c di gmp c di amp cadpr cgamp nucleoside diphosphate adp gdp m 5 udp udp cdp xanthosine diphosphate dadp dgdp dtdp dudp dcdp nucleoside triphosphate atp gtp m 5 utp utp ctp itp xtp datp dgtp dttp dutp dctp ditp dxtp this biochemistry article is a stub you can help wikipedia by adding missing information v t e retrieved from https en wikipedia org w index php title thymidine_diphosphate oldid 1372337933 categories nucleotides pyrophosphate esters thymine derivatives biochemistry stubs hidden categories articles without kegg source articles with changed ebi identifier articles containing unverified chemical infoboxes articles with short description short description matches wikidata all stub articles this page was last edited on 31 august 2026 at 09 09 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents thymidine diphosphate 13 languages add topic