DMAPP (ammonium salt)
(Synonyms: 二甲基烯丙基二磷酸三铵盐,Dimethylallyl Pyrophosphate) 目录号 : GC43502DMAPP(二甲基焦磷酸烯丙基)是生物源类异戊二烯合成过程中一个关键的类异戊二烯前体。
Cas No.:1186-30-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
DMAPP (Dimethylallyl pyrophosphate) serves as a pivotal isoprenoid precursor within the realm of biogenic isoprenoid synthesis. It finds its origin as a metabolic product originating from two primary pathways: the mevalonate pathway and the MEP (2-C-methyl-D-erythritol 4-phosphate) pathway, both being prominent conduits for isoprenoid precursor biosynthesis in diverse biological systems. Remarkably, DMAPP stands as an isomeric counterpart to isopentenyl pyrophosphate (IPP), constituting a prevalent molecular entity that ubiquitously permeates the living kingdom[1-2].
References:
[1]. Mus AA, Goh LPW, Marbawi H, Gansau JA. The Biosynthesis and Medicinal Properties of Taraxerol. Biomedicines. 2022 Mar 30;10(4):807. doi: 10.3390/biomedicines10040807. PMID: 35453556; PMCID: PMC9025716.
[2]. Wang W, Oldfield E. Bioorganometallic chemistry with IspG and IspH: structure, function, and inhibition of the [Fe(4)S(4)] proteins involved in isoprenoid biosynthesis. Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4294-310. doi: 10.1002/anie.201306712. Epub 2014 Jan 31. PMID: 24481599; PMCID: PMC3997630.
DMAPP(二甲基焦磷酸烯丙基)是生物源类异戊二烯合成过程中一个关键的类异戊二烯前体。它起源于两个主要途径的代谢产物:甲羟戊酸途径和MEP (2-C-methyl-D-erythritol 4-phosphate)途径,两者都是不同生物系统中类异戊二烯前体生物合成的重要通道。值得一提的是,DMAPP作为焦磷酸异戊烯基(IPP)的异构体,在生物中普遍存在[1-2]。
| Cas No. | 1186-30-7 | SDF | |
| 别名 | 二甲基烯丙基二磷酸三铵盐,Dimethylallyl Pyrophosphate | ||
| Canonical SMILES | [O-]P([O-])(OP([O-])(OC/C=C(C)\C)=O)=O.[NH4+].[NH4+].[NH4+] | ||
| 分子式 | C5H12O7P2•3(NH4) | 分子量 | 297.2 |
| 溶解度 | NH4OH (7:3): 2 mg/ml; Water: 25 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3647 mL | 16.8237 mL | 33.6474 mL |
| 5 mM | 0.6729 mL | 3.3647 mL | 6.7295 mL |
| 10 mM | 0.3365 mL | 1.6824 mL | 3.3647 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synthesis and enzymatic studies of bisubstrate analogues for farnesyl diphosphate synthase
J Org Chem 2015 Apr 17;80(8):3902-13.PMID:25734506DOI:10.1021/acs.joc.5b00202
Farnesyl diphosphate synthase catalyzes the sequential chain elongation reactions between isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) to form geranyl diphosphate (GPP) and between IPP and GPP to give farnesyl diphosphate (FPP). Bisubstrate analogues containing the allylic and homoallylic substrates were synthesized by joining fragments for IPP and the allylic diphosphates with a C-C bond between the methyl group at C3 in IPP and the Z-methyl group at C3 in DMAPP (3-OPP) and GPP (4-OPP), respectively. These constructs placed substantial limits on the conformational space available to the analogues relative to the two substrates. The key features of the synthesis of bisubstrate analogues 3-OPP and 4-OPP are a regioselective C-alkylation of the dianion of 3-methyl-3-buten-1-ol (5), a Z-selective cuprate addition of alkyl groups to an α,β-alkynyl ester intermediate, and differential activation of allylic and homoallylic alcohols in the analogues, followed by a simultaneous displacement of the leaving groups with tris(tetra-n-butylammonium) hydrogen diphosphate to give the corresponding bisdiphosphate analogues. The bisubstrate analogues were substrates for FPP synthase, giving novel seven-membered ring analogues of GPP and FPP. The catalytic efficiencies for cyclization of 3-OPP and 4-OPP were similar to those for chain elongation with IPP and DMAPP.