ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(6R,S)-5-Formyl-6-methyl-5,6,7,8-tetrahydropterine: Synthesis, Chemical and Physico-chemical Properties(6R, S)-5-Formyl-6-methyl-5,6,7,8-tetrahydropterine (III), a model substance for the biologically important 6-substituted 5-formyl-5,6,7,8-tetrahydropterines, was obtained for the first time by formylation of the corresponding tetrahydropterine with formic acid. Compound III, analogously to the other known 5-acyltetrahydropterines, exists in solution (except in DMSO) as a mixture of two rotamers IIIa and IIIb. The two H-C(7) in III have the same chemical shift and the same coupling constant to H-C(6), giving rise to a A,A',X,C-system. Conformational analysis of III, based on its 1H-NMR,-spectrum, shows that the methyl group is pseudo-axial and the formyl group pseudo-equatorial. Moreover, the H(X)-C(6) bond lies nearly in the plane bisecting the C(6)-C(7)-H(A), C(6)-C(7)-H(A') dihedral angle; the C(6) and C(7) lie outside the N(5)-C(4a)-C(8a) plane and the tetrahydropyrazine cycle must be extremely strained, according to Dreiding models.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640138
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