Adenosine thiamine diphosphate

Adenosine thiamine diphosphate (AThDP), or thiaminylated adenosine diphosphate (ADP) is a naturally occurring thiamine adenine nucleotide. It was chemically synthesized and exists in small amounts in vertebrate liver. Its biological significance remains unknown.[1][2]

Adenosine thiamine diphosphate
Names
Systematic IUPAC name
(22R,23S,24R,25R)-16,134-Diamino-23,24,5,7-tetrahydroxy-114,132-dimethyl-5,7-dioxo-4,6,8-trioxa-5λ5,7λ5-diphospha-113λ5-1(9)-purina-13(5)-pyrimidina-11(5,3)-[1,3]thiazola-2(2,5)-oxolanatridecaphan-113-ylium
Identifiers
3D model (JSmol)
  • InChI=1S/C22H29N9O10P2S/c1-11-15(44-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-38-42(34,35)41-43(36,37)39-7-14-17(32)18(33)22(40-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H5-,23,24,25,26,27,29,34,35,36,37)/p+1/t14-,17+,18+,22-/m1/s1
    Key: YLSJMTRFGUMRTH-HPXJRWHBSA-O
  • acid: CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCOP(=O)(O)OP(=O)(O)OC[C@@H]3[C@@H]([C@@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O
Properties
C22H28N9O10P2S
Molar mass 674.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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See also

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References

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  1. ^ Bettendorff L (November 2021). "Update on Thiamine Triphosphorylated Derivatives and Metabolizing Enzymatic Complexes". Biomolecules. 11 (11): 1645. doi:10.3390/biom11111645. PMC 8615392. PMID 34827643.
  2. ^ Frédérich M.; Delvaux D.; Gigliobianco T.; Gangolf M.; Dive G.; Mazzucchelli G.; Elias B.; De Pauw E.; Angenot L.; Wins P.; Bettendorff L. (2009). "Thiaminylated adenine nucleotides — chemical synthesis, structural characterization and natural occurrence FEBS J.". The FEBS Journal. 276 (12): 3256–3268. doi:10.1111/j.1742-4658.2009.07040.x. PMID 19438713. S2CID 23313946.