Zur Chemie der „energiereichen Phosphate”︁, XVI<sup>1)</sup> Die Synthese der Argininphosphorsäure und die Reaktion von Isoureidophosphonaten mit Aminen

Cramer, Friedrich; Scheiffele, Ekkehard; Vollmar, Arnulf

doi:10.1002/cber.19620950715

Cited by 13 publications

(5 citation statements)

References 31 publications

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“…It is also worth noting that preparations of phosphoarginine, whether by extraction from muscle, synthetic or enzymatic, most commonly involve precipitation of barium salts from ethanol-water mixtures (the synthesis of Cramer et al [68] above is an exception), whereas Bolte and Whitesides [73] found it more convenient to isolate the phosphoarginine as the neutral species (19c in Fig. 22).…”

Section: Synthesismentioning

confidence: 96%

“…Cramer et al [68] also synthesised phosphoarginine by treating ornithine (34) with the O-methyl-N-phosphorylisourea (35) under basic conditions (Fig. 23).…”

Section: Synthesismentioning

confidence: 97%

“…(22). An efficient synthesis of phosphoarginine using a traditional protecting group strategy [68]. Fig.…”

Section: Synthesismentioning

confidence: 99%

“…(23). Synthesis of phosphoarginine (19e represents the fully deprotonated form) from ornithine (34) [68]. See Fig.…”

Section: Synthesismentioning

confidence: 99%

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Focus on Phosphoarginine and Phospholysine

Besant

Attwood

Piggott

2009

CPPS

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Protein phosphorylation is a common signaling mechanism in both prokaryotic and eukaryotic organisms. Whilst serine, threonine and tyrosine phosphorylation dominate much of the literature there are several other amino acids that are phosphorylated in a variety of organisms. Two of these phosphoamino acids are phosphoarginine and phospholysine. This review will focus on the chemistry and biochemistry of both phosphoarginine and phospholysine. In particular we focus on the biological aspects of phosphoarginine as a means of storing and using metabolic energy (in place of phosphocreatine in invertebrates), the chemistry behind its synthesis and we examine the chemistry behind its highenergy phosphoramidate bond. In addition we will be reporting on the incidence of phosphoarginine in mammalian cells. Similarly we will be reviewing the current findings on the biology and the chemistry of phospholysine and its involvement in a variety of biological systems.

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Section: Synthesismentioning

confidence: 96%

“…Cramer et al [68] also synthesised phosphoarginine by treating ornithine (34) with the O-methyl-N-phosphorylisourea (35) under basic conditions (Fig. 23).…”

Section: Synthesismentioning

confidence: 97%

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Focus on Phosphoarginine and Phospholysine

Besant

Attwood

Piggott

2009

CPPS

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“…Synthetic access to specifically modified peptides has proven to be an important tool for the study of PTMs but current methods for arginine phosphorylation are either unspecific 13 or designed to prepare pArg as the free amino acid. 14,15 To overcome this limitation we here present the synthesis of peptides containing specific pArg residues by solid phase peptide synthesis (SPPS). For this building block approach the choice of protecting groups for the phosphoguanidinium moiety is crucial.…”

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confidence: 99%