2-(1-Methylguanidino)ethyl Dihydrogen Phosphate , Aplodan

This guanidine phosphate salt derivative is a white to pale yellow crystalline powder that decomposes at 244°C.Its predicted density is 1.65 g/cm³,and it requires storage at-20°C to ensure the stability of the phosphate ester bond and the guanidino group.The compound is slightly soluble in water but exhibits good solubility in polar organic solvents such as methanol,ethanol,DMF,and acetone.The guanidino group(-C(NH)NH₂)is strongly basic,while the dihydrogen phosphate moiety is acidic,potentially allowing it to exist as an inner salt in solution.Contact with strong oxidizers,acids,and bases should be avoided to prevent hydrolysis of the phosphate ester or irreversible chemical changes to the guanidine group.

2-[Carbamimidoyl(methyl)amino]ethyl dihydrogen phosphate is a structurally unique precursor for bioactive phosphates.Its molecule integrates three key pharmacophores:a guanidine unit(mimicking an arginine side chain,participating in ionic and hydrogen bonding interactions),a tertiary amine linker(providing spatial separation and a potential protonation site),and a terminal dihydrogen phosphate(serving as a polar head group or phosphorylation precursor).This polyionic structure makes it an important synthon for mimicking phosphorylated amino acid or nucleotide fragments,holding special value in probe design and prodrug development.

1.Pharmaceutical Synthesis

Serves as a key building block for phosphorylated mimics of Cell-Penetrating Peptides(CPPs),used to enhance the cell membrane permeability of oligonucleotide or peptide drugs.Its guanidino group can mimic the membrane translocation function of arginine,while the phosphate ester can be enzymatically cleaved intracellularly to release the active payload.Also used in synthesizing bioactive probes targeting phosphokinases or phosphatases,and as a synthetic precursor for nucleotide analogs in antiviral and antitumor drug research.

2.Agrochemical R&D

Explored as a synthetic intermediate for novel plant growth regulators or Systemic Acquired Resistance(SAR)inducers.Its phosphoguanidine structure may mimic charged fragments of plant defense signaling molecules(e.g.,oligogalacturonides),potentially activating plant immune responses to improve crop resistance against pathogens.Also used in designing systemic fungicide or insecticide prodrugs to enhance foliar uptake and translocation.

3.Functional Material Synthesis

Acts as a zwitterionic monomer or surface modifier for preparing biocompatible coatings resistant to protein adsorption(e.g.,for medical devices).Its simultaneous positive and negative charges can form a dense hydration layer,effectively reducing non-specific biofouling.Furthermore,it can be used to synthesize pH-responsive smart hydrogels,whose swelling/contraction behavior changes with environmental pH due to altered charge states.

4.Organic Synthesis Building Block

Functions as a multifunctional,polar linker with orthogonal protecting groups in Solid-Phase Peptide Synthesis(SPPS)or oligonucleotide synthesis for introducing phosphorylation or guanidinylation modifications.Its guanidine group can form amidine bonds with carbonyl compounds,serving as a unique handle for bioconjugation chemistry.Also serves as a model compound for studying the conformation and ionic interactions of phosphoguanidine-type molecules in solution.