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1.
Configuration and conformation of 6,7-Dimethyl- and 5,6,7-Trimethyl-5,6,7,8-tetrahydropterines. During the hydrogenation of 6,7-dimethylpterine, cis-6,7-dimethyl-tetrahydropterine is formed. A possible conformation for this substance and for the 5,6,7-trimethyl derivative, which is obtained from it, is discussed, taking the 1H-NMR. spectra of both tetrahydropterines into consideration. 相似文献
2.
The crystal structure of 5-formyl-6,7-dimethyl-5,6,7,8-tetrahydropterine The crystal structure of the title compound, a tetrahydropterine, has been determined by X-ray analysis (direct method) and refined with 1579 structure amplitudes to R = 0.054. The crystal system is triclinic, space group P1 , with unit cell dimensions a = 7.171, b = 7.255, c = 12.369 Å, α = 100.64, β = 93.32, γ = 98.27°. The tetrahydropyrazine ring exists in a distinctly flattened conformation. The C(13)- and C(14)-CH3-groups possess a cis-configuration with axial position for C(13)-CH3 and equatorial for C(14)-CH3. The carbonyl-group of the N-formyl function has an (E)-configuration. 相似文献
3.
The crystal structure of xanthopterine-hydrochloride. The crystal structure of the title compound, a pterine, has been determined by X-ray analysis (direct methods) and refined with 1332 structure amplitudes to R = 0.027. The crystal system is monoclinic, space group P21/c, with unit cell dimensions a = 7.942, b = 8.417, c = 12.076 Å, β = 93.77°. The molecule is protonated at the N(1)-position. The angle between the planes of the pyrimidine and pyrazine rings is 2.02°. 相似文献
4.
Starting with 5-formyl-6,7-dimethyl-5,6,7,8-tetrahydropterine (II), a new synthesis of 5,6,7-trimethyl-5,6,7,8-tetrahydropterine (III) is described. Thereby the chemical behaviour of the 5-formyl group in II is investigated, in order to enable the unequivocal differentiation between formylation at position 5 and at position 10 in folic and tetrahydrofolic acid derivatives. 13C-NMR. spectra of II and III are discussed. 相似文献
5.
Jost H. Bieri 《Helvetica chimica acta》1977,60(7):2303-2308
The crystal structure of 6-methyl-7,8-dihydropterine-monohydrochloride-monohydrate The crystal structure of the title compound has been determined by X-ray analysis (direct methods) and refined with 990 structure amplitudes to R = 0.025. The crystal system is triclinic, space group P1 , with unit cell dimensions a = 5.859, b = 7.686, c = 12.107, α = 71.84, β = 76.35, γ = 85.80. The molecule is protonated at the N(5)-position and is planar. The atoms H(19) and H(20) are with 0.818 Å above respectively with ?0.705 Å under the plane. 相似文献
6.
Conformational Analysis of Acylated 5,6,7,8-Tetrahydropterines The conformation of N(5)-acetates, and of N(5)- and N(8)-trifluoroacetates, respectively, of 6-methyl- and cis-6, 7-dimethyl-tetrahydropterines is studied by 1H-NMR. spectroscopy. It is shown that the methyl group next to the acylated nitrogen atom is in quasi-axial position. 相似文献
7.
Synthesis of 7-Aminoxanthopterin 7-Aminoxanthopterin (II) is obtained in good yield and purity by the transformation of isomer-free xanthopterin-7-carboxylic acid (I) with NH3 followed by oxidation with MnO2. The Frontier Orbital Theory contributes to a better understanding of the reaction pathway. 相似文献
8.
Conformational analysis of 5,6,7,8-tetrahydropteroic acid and 5,6,7,8-tetrahydro-L -folic acid In the 360-MHz-1H-NMR.-spectrum of (6R, S)-9,9-dideuterio-5, 6, 7, 8-tetrahydropteroic acid (racemic) (XIII) (AMX-System, Fig. 4) and (6R, S)-9,9-dideuterio-5, 6, 7, 8-tetrahydro-L -folic acid (diastereomeric) (XVI) the Ha–C(6) and Ha–C(7) show a vicinal coupling constant of 6,7 Hz and the Ha–C(6) and He–C(7) one of 3,2 Hz. The first coupling constant provides evidence for an approximate trans-diaxal arrangement of Ha–C(6) and Ha–C(7), and the second for a gauche conformation of Ha–C(6) and He–C(7). The tetrahydropyrazine ring in the racemic 5, 6, 7, 8-tetrahydropteroic acid (III) and in the diastereomeric 5, 6, 7, 8-tetrahydro-L -folic acid (XVII) exists therefore in a half-chair conformation with a pseudoequatorial position of the side chain at C(6) (Fig.5). 相似文献
9.
Roland Prewo Jost H. Bieri Subhendu Narayan Ganguly Max Viscontini 《Helvetica chimica acta》1982,65(3):1094-1099
The Configuration at C(6) of Natural 5,6,7,8-Tetrahydro-L-biopterin and of its Pentaacetate The structure of (6.R)-pentaacetyl-5,6,7,8-tetrahydro-L-biopterin, one of two diastereoisomers obtained by catalytic hydrogenation and subsequent acetylation of L-biopterin, has been determined by X-ray diffraction analysis. The space group is P212121, a=8,053(l), b=14,955(3), c= 21,502 (4) Å. The asymmetric unit contains one molecule of the biopterin derivative and one of ethyl acetate. The R-configuration can be assigned to C(6) by reference to the known configurations of the other asymmetric C-atoms. As hydrolysis of this diastereoisomer yields the natural 5, 6,7,8-tetrahydro-L-biopterin, the latter also possesses the (6 R)-configuration. 相似文献
10.
Preparation of (6RS)Tetra- and (6RS)-Pentaacetyl-5,6,7,8-tetrahydro-L-biopterines Boiling of (6RS) l′-O,2′-O,2-N-triacetyl-5,6,7,8-tetrahydro-L-biopterine in acetic anhydride as described in [2], leads to a mixture of the diastereoisomeric (6R)- and (65)-l′-O,2′-O,2-N-,5,8-pentaacetyl-5,6,7,8-L,-biopterines. One of the diastereoisomers can be obtained as pure crystals. It corresponds to the pentaacetate of the natural (6R)- or (6S).,5,6,7,8-tetrahydro-L-biopterine. For the preparation of the earlier described (6RS)- and (6S)-tetraacetyl-tetrahydro-L-biopterines [2] improved conditions are reported. 相似文献
11.
Sterochemical Properties of the Acylated 5,6,7,8-Tetrahydropterines. Rotameres of the 5-Trifluoroacetyl-tetrahydropterine Derivatives 6-Methyl- and 6,7-dimethyl-5,6,7,8-tetrahydropterine are acylated with the anhydrides of acetic acid and trifluoroacetic acid. It is shown that the reactivity of the nitrogen otoms increases in the following order: N(3), N(8), N(2′) and N(5). Two rotameres are present in the 1H-NMR. spectra of the N(5)-trifluoroacetates, but not in those of the N(5)-acetates. 相似文献
12.
13.
Polyacetylated 5,6,7,8-Tetrahydro-D - and L -neopterins. A Special Case of N(5)-Alkylation of 5,6,7,8-Tetrahydroneopterins Improved conditions are reported for the preparation of the earlier described (6R)- and (6S)-1′-O,2′-O,3′-O,2-N,5-pentaacetyl-5,6,7,8-tetrahydro-L -neopterins, one of which could be obtained as pure crystals. Its structure, determined by X-ray-diffraction analysis, corresponds to the (6R)-enantiomer. The method has also been used to make the corresponding D -diastereoisomers. Further acetylation of (6RS)-1′-O,2′-O,3′-O,2-N-tetraacetyl-5,6,7,8-tetrahydro-D -neopterin under drastic conditions yields a mixture of several polyacetylated D -neopterin derivatives and a polyacetylated ethyl-tetrahydro-D -neopterin which was isolated in crystalline form and established by X-ray-diffraction analysis to be (6R)-1′-O,2′-O,3′-O,4-O,2-N,2-N,8-heptaacetyl-5-ethyl-5,6,7,8-tetrahydro-D -neopterin. 相似文献
14.
Esam Khalifa Abhoy N. Ganguly Jost H. Bieri Max Viscontini 《Helvetica chimica acta》1980,63(8):2554-2558
A Convenient Synthesis of Leucovorin The synthesis of leucovorin, a 5-formyl-(6R or S)-5,6,7,8-tetrahydropteroyl-L -glutamic acid (II) is described. The L -folic acid was first reduced to (6R, S)-tetrahy-dro-L -folic acid (I); formylation with methyl-formate in DMSO gave directly leucovorin (as a diastereomeric mixture) in good yields. To demonstrate, that the formylation occurred regiospecifically at N (5) and not at N (10), N (10)-nitroso-(6 R, S)-tetrahydro-L -folic acid was formylated under the same conditions. Reductive elimination of the N (10)-nitrosogroup gave the identical leucovorin as in the previous case. The synthetic leucovorin was biologically as active as the natural product with Streptococcus faecalis ATCC 8043 and Pediococcus cerevisiae ATCC 8081. 相似文献
15.
Abhoy N. Ganguly Pradip K. Sengupta Jost H. Bieri Max Viscontini 《Helvetica chimica acta》1980,63(6):1754-1758
On the Pathway of the Catalytic Reduction of 6-Methylpterin The catalytic hydrogenation of 6-methylpterin (I) in neutral or weekly acidic solution begins, as for the 7-methylpterin, by the thermodynamically controlled reduction of the 7,8-double bond. It is not possible to say, according to our experiments, which double bound, either the 5,6 or the 7,8, is first reduced in strongly acidic solution. However, a 5,8-reduction can be excluded. 相似文献
16.
17.
A. Bobst 《Helvetica chimica acta》1967,50(8):2222-2225
EPR. investigations show the existence of one-electron oxidation of 5,6,7,8-tetrahydropterine and tetrahydrofolic acid resulting in unstable cationic radicals of red color which are trapped at liquid nitrogen temperature. 相似文献
18.
Esam Khalifa Hans-Jürg Furrer Jost H. Bieri Max Viscontini 《Helvetica chimica acta》1978,61(7):2739-2743
Regiospecific deuteriation of folic acid Introduction of a nitroso function at the N (10)-position of folic acid activates the C(9)-hydrogen atoms in such a way, that the exchange of H with D at this position, in NaOD-solution, is extremely facilitated. This fact is utilized in the synthesis of 9,9-dideuterio-folic acid (IV), 7,9,9-trideuterio-folic acid (VII) and 7-deuterio-folic acid (IX). These three products are necessary for the 1H-NMR.-spectroscopical determination of the conformation of 5,6,7,8-tetrahydrofolic acid and its derivatives. 相似文献
19.
A. Ehrenber P. Hemmerich F. Müller T. Okada M. Viscontini 《Helvetica chimica acta》1967,50(2):411-416
By oxydation of N(5)-methyl-6,7-diphenyl-5,6-dihydro- and N(5)-methyl-6,7-diphenyl-5,6,7,8-tetrahydro-pterine derivatives with perhydrol 8-monohydro- and 6,7,8-trihydro-pteridine radical cations are produced which are sufficiently stable for detection and structural elucidation by ESR. hyperfine analysis. The biological implications of these radicals for pteridine dependent hydroxylation and methyl transfer from 5-methylfolinic acid are discussed. 相似文献