1D-myo-inositol 1,2,3,5,6-pentakisphosphate

Base Information

• Chemical Name: 1D-myo-inositol 1,2,3,5,6-pentakisphosphate
• CAS No.: 26326-85-2
• Molecular Formula: C6H17O21P5
• Molecular Weight: 580.057
• UNII: EA52J6WT2B
• DSSTox Substance ID: DTXSID10470896
• Metabolomics Workbench ID: 52480
• Nikkaji Number: J885.458K
• Wikidata: Q27104611
• Mol file: 26326-85-2.mol

Synonyms:(D)-isomer, specified as 1,2,4,5,6 of inositol pentaphosphate;inositol pentakisphosphate;inositol pentaphosphate;inositol pentis(dihydrogen phosphate);InsP5;myo-inositol 1,3,4,5,6-pentakisphosphate;myo-inositol pentakis(dihydrogen phosphate)

Chemical Property of 1D-myo-inositol 1,2,3,5,6-pentakisphosphate

Chemical Property:

• PSA: 403.08000
• LogP: -3.24960
• Storage Temp.: ?20°C
• XLogP3: -9.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 10
• Exact Mass: 579.89504254
• Heavy Atom Count: 32
• Complexity: 824

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-myo-Inositol 1,2,3,5,6-pentakis-phosphate ≥80% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(C(C(C(C(C1OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)O
• Isomeric SMILES: [C@H]1([C@H](C([C@@H]([C@@H](C1O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O
• Uses: myo-Inositol 1,2,3,5,6-pentakisphosphate regulates RNA polymerase I-mediated rRNA transcription in Saccharomyces cerevisiae.

Technology Process of 1D-myo-inositol 1,2,3,5,6-pentakisphosphate

There total 10 articles about 1D-myo-inositol 1,2,3,5,6-pentakisphosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

sodium inositol hexaphosphate (17211-15-3) → Ins(1,2,3,4,6)P5 (26326-85-2)

Guidance literature:

With acetate buffer; at 35 ℃; for 0.5h;

DOI:10.1021/jf025620t

Reference yield:

Benzoic acid (1S,2S,3R,4S,5R,6R)-2,3,4,5,6-pentakis-phosphonooxy-cyclohexyl ester → Ins(1,2,3,4,6)P5 (26326-85-2)

Guidance literature:

With lithium hydroxide; at 80 ℃; for 3h;

DOI:10.1016/S0960-894X(98)00245-5

Reference yield:

(±)-1,2:5,6-di-O-isopropylidene-myo-inositol (38643-30-0,40617-60-5,42973-31-9,65556-81-2,96092-79-4,96092-80-7,115116-18-2,115116-20-6) → Ins(1,2,3,4,6)P5 (26326-85-2)

Guidance literature:

Multi-step reaction with 8 steps

1: lipase from Candida rugosa (sigma, CRL) / diethyl ether / Ambient temperature

2: LiOH / methanol; H₂O / 0 °C

3: pyridine

4: 80percent aq. AcOH / 1 h / 100 °C

5: iPr₂NEt / dimethylformamide

6: 30percent aq. H₂O₂

7: TMSBr / CH₂Cl₂

8: 1 N LiOH / 3 h / 80 °C

With pyridine; lithium hydroxide; trimethylsilyl bromide; lipase from Candida rugosa (sigma, CRL); dihydrogen peroxide; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(98)00245-5

upstream raw materials:

sodium inositol hexaphosphate

(1R,2S,3S,4R)-2,3,4-tri-O-acetyl-1-O-benzylconduritol B

(±)-1,2:5,6-di-O-isopropylidene-myo-inositol

Acetic acid (3aR,4R,5S,5aR,8aR,8bS)-5-hydroxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester

Downstream raw materials:

myo-Inositol 2-phosphate

D-myo-inositol 1,2,6-trisphosphate

Refernces

• 1、 Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef. "Flexible stereo- and regioselective synthesis of myo-inositol phosphates (Part 2): Via nonsymmetrical conduritol B derivatives". . p. 3116 - 3127. Retrieved 2007/10/03.
• 2、 Nakano, Tadao,Joh, Toshio,Narita, Kazumasa,Hayakawa, Toshiro. "The pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases from wheat bran of Triticum aestivum L. cv. Nourin #61". . p. 995 - 1003. Retrieved 2007/10/03.