Pterin

Structural formula
General
Surname	Pterin
other names	2-amino-3 H -pteridin-4-one
Molecular formula	C 6 H 5 N 5 O
Brief description	beige to yellow crystalline solid
External identifiers / databases
EC number	218-799-1
ECHA InfoCard	100.017.091
PubChem	73000
ChemSpider	65806
Wikidata	Q386702
properties
Molar mass	163.14 g mol −1
Physical state	firmly
Melting point	> 360 ° C
pK s value	pK s 1 2.20 (20 ° C); pK s 2 7.86 (20 ° C);
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pterine is a derivative of pteridine and therefore a heterocyclic compound. It occurs as a structural element in many biomolecules, e.g. B. in various color pigments of insects such as leucopterin and xanthopterin , in the cofactor biopterin or in the vitamin folic acid .

properties

Pterin forms light yellow crystals . When heated, it decomposes without melting. The compound shows two acid constants with pK _{s ₁} 2.20 and pK _{s ₂} 7.86 (in water at 20 ° C.). The solubility in water is 0.175 g * l ⁻¹ .

The compound can occur in two tautomeric structures.

synthesis

Pterin is produced by reacting methyl 3-chloropyrazine-carboxylate with guanidinium hydrogen carbonate.

Another synthesis starts from 2,4,5-triamino-6-hydroxypyrimidine, which is reacted with glyoxal .

Individual evidence

↑ Pterin data sheet at Acros, accessed on July 2, 2007.
^ Entry on pteridines. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
↑ ^a ^b ^c Pfleiderer, W .; Liedek, E .; Lohrmann, R .; Rukwied, M .: Pteridine, X. On the structure of pterin in Chem. Ber. 93 (1960) 2015-2022. doi : 10.1002 / cber.19600930916 .
↑ ^a ^b Data sheet Pterine at Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
↑ Albert et al .: J. Chem. Soc. 1952, 4219-4220.
↑ Jaramillo, P .; Coutinho, K .; Canuto, S .: Solvent Effects in Chemical Processes. Water-Assisted Proton Transfer Reaction of Pterin in Aqueous Environment in J. Phys. Chem. A 113 (2009) 12485-12495. doi : 10.1021 / jp903638n .
^ GPG Dick, HCS Wood: Pteridine derivatives. Part I. A new synthesis of 2-amino-4-hydroxypteridines. In: Journal of the Chemical Society (Resumed). 1955, p. 1379, doi : 10.1039 / JR9550001379 .
Jump up ↑ JH Mowat, JH Boothe, BL Hutchings, ELR Stokstad, CW Waller, RB Angier, J. Semb, DB Cosulich, Y. SubbaRow: The Structure of the Liver L. casei Factor in J. Am. Chem. Soc. 70 (1948) 14-18, doi : 10.1021 / ja01181a005 .

[Acros-1] Pterin data sheet at Acros, accessed on July 2, 2007.

[2] Entry on pteridines. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[pfeidlerer-3] Pfleiderer, W .; Liedek, E .; Lohrmann, R .; Rukwied, M .: Pteridine, X. On the structure of pterin in Chem. Ber. 93 (1960) 2015-2022. doi : 10.1002 / cber.19600930916 .

[Sigma-4] Data sheet Pterine at Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[5] Albert et al .: J. Chem. Soc. 1952, 4219-4220.

[6] Jaramillo, P .; Coutinho, K .; Canuto, S .: Solvent Effects in Chemical Processes. Water-Assisted Proton Transfer Reaction of Pterin in Aqueous Environment in J. Phys. Chem. A 113 (2009) 12485-12495. doi : 10.1021 / jp903638n .

[7] GPG Dick, HCS Wood: Pteridine derivatives. Part I. A new synthesis of 2-amino-4-hydroxypteridines. In: Journal of the Chemical Society (Resumed). 1955, p. 1379, doi : 10.1039 / JR9550001379 .

[8] Jump up ↑ JH Mowat, JH Boothe, BL Hutchings, ELR Stokstad, CW Waller, RB Angier, J. Semb, DB Cosulich, Y. SubbaRow: The Structure of the Liver L. casei Factor in J. Am. Chem. Soc. 70 (1948) 14-18, doi : 10.1021 / ja01181a005 .