Lombricine

Lombricine
	D-lombricine
Names
	IUPAC name O-[{2-[(Diaminomethylene)amino]ethoxy}(hydroxy)phosphoryl]-D-serine
	Other names D-Lombricine
Identifiers
CAS Number	79342-60-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32969;
ChemSpider	388647;
PubChem CID	439556;
UNII	YMK242B63W ;
CompTox Dashboard (EPA)	DTXSID101156421 ;
	InChI InChI=1S/C6H15N4O6P/c7-4(5(11)12)3-16-17(13,14)15-2-1-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H,13,14)(H4,8,9,10)/t4-/m1/s1 Key: GSDBGCKBBJVPNC-SCSAIBSYSA-N; InChI=1/C6H15N4O6P/c7-4(5(11)12)3-16-17(13,14)15-2-1-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H,13,14)(H4,8,9,10)/t4-/m1/s1 Key: GSDBGCKBBJVPNC-SCSAIBSYBR;
	SMILES O=C(O)[C@H](N)COP(=O)(OCC/N=C(\N)N)O;
Properties
Chemical formula	C6H15N4O6P
Molar mass	270.182 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lombricine is a phosphagen that is unique to earthworms. Structurally, it is a phosphodiester of 2-guanidinoethanol and the amino acid serine and is found in both enantiomeric forms. In many worm species it is further phosphorylated by lombricine kinase to N-phospholombricine.^[1]^[2]

Metabolism

Lombricine kinase is the enzyme first characterised from the worm species, Lumbricus terrestris, that converts lombricine to N-phospholombricine using adenosine triphosphate (ATP) as the source of the transferred phosphate group.^[3]

2D representation of the chemical structure of Q27101985.

L-lombricine

ATP

ADP

Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right

2D representation of the chemical structure of Q27102786.

N-phospho-L-lombricine

The enzyme is found widely in annelids, where D-lombricine is the favoured form but some marine worms (echiuroids) contain L-lombricine derived from L-serine.^[2]^[4]

References

↑ Rossiter, RJ; Gaffney, TJ; Rosenberg, H; Ennor, AH (1960). "The formation in vivo of lombricine in the earthworm (Megascolides cameroni)". The Biochemical Journal. 76 (3): 603–10. doi:10.1042/bj0760603. PMC 1204840. PMID 13743749.
1 2 Petkowski, Janusz J.; Bains, William; Seager, Sara (2019). "Natural Products Containing 'Rare' Organophosphorus Functional Groups". Molecules. 24 (5): 866. doi:10.3390/molecules24050866. PMC 6429109. PMID 30823503.
↑ Ellington, W Ross (2001). "Evolution and Physiological Roles of Phosphagen Systems". Annual Review of Physiology. 63: 289–325. doi:10.1146/annurev.physiol.63.1.289. PMID 11181958.
↑ van Thoai N, Robin Y, Guillou Y (1972). "A new phosphagen, N'-phosphorylguanidinoethylphospho-O-( -N,N-dimethyl)serine (phosphothalassemine)". Biochemistry. 11 (21): 3890–5. doi:10.1021/bi00771a009. PMID 5079888.

[1] Rossiter, RJ; Gaffney, TJ; Rosenberg, H; Ennor, AH (1960). "The formation in vivo of lombricine in the earthworm (Megascolides cameroni)". The Biochemical Journal. 76 (3): 603–10. doi:10.1042/bj0760603. PMC 1204840. PMID 13743749.

[Petkowski-2] 1 2 Petkowski, Janusz J.; Bains, William; Seager, Sara (2019). "Natural Products Containing 'Rare' Organophosphorus Functional Groups". Molecules. 24 (5): 866. doi:10.3390/molecules24050866. PMC 6429109. PMID 30823503.

[3] Ellington, W Ross (2001). "Evolution and Physiological Roles of Phosphagen Systems". Annual Review of Physiology. 63: 289–325. doi:10.1146/annurev.physiol.63.1.289. PMID 11181958.

[4] van Thoai N, Robin Y, Guillou Y (1972). "A new phosphagen, N'-phosphorylguanidinoethylphospho-O-( -N,N-dimethyl)serine (phosphothalassemine)". Biochemistry. 11 (21): 3890–5. doi:10.1021/bi00771a009. PMID 5079888.

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