ISSN:
0899-0042
Keywords:
1-[4-[[1-(2-amino-7-methyl-4-hydroxo-6-pteridinyl)ethyl]amino]phenyl]-1-deoxy-D-ribitol
;
(S)-6-[1-(4-carboxymethyllanilino)ethyl]pterin
;
D(+)-neopterin
;
L-biopterin
;
(S)-6-(1-hydroxyethyl)pterin
;
(S)-6-(1-hydroxyethyl)-7-methylpterin
;
(R)-6-(1-phenoxyethyl)pterin
;
stereospecific synthesis
;
circular dichroism
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The configuration at the C-9 of methanopterin (MPT) has been determined by comparing the circular dichroism (CD) spectra of MPT and its hydrolytic fragment, 1-[4-[[1-(2-amino-7-methyl-4-hydroxy-6-pteridinyl)-ethyl]amino]phenyl]-1-deoxy-D-ribitol (HP-1), with the CD spectra of a series of model compounds of known stereochemistry. These compounds included (S)-6-[1-(4-carboxymethylanilino)ethyl]pterin, (S-6(1-hydroxyethyl)-7-methylpterin, (S-6-(1-hydroxyethyl)pterin, (R)-6-(1-phenoxyethyl)pterin, D(+)-neopterin, and L-biopterin. From this comparison it was concluded that MPT has the R configuration at C-9 and is thus configurationally related to D(+)-neopterin, which has the S configuration at C-1. From previous work establishing the relative stereochemistry at C-6, C-7, and C-9 of N5-N10-methenyl-5,6,7,8-tetrahydromethanopterin (N5-N10-methenyl-H4MPT) as R, S, and R, respectively, it is clear that the remaining asymmetric carbons at C-6 and C-7 of H4MPT have the S and S configuration, respectively. Comparison of these latter two positions to the equivalent carbons in 5,6,7,8-tetrahydrofolate (H4folate) show that the steps involved in the biological reduction of MPT to H4MPT occur with the same stereochemical outcome as those involved in the biological reduction of folate to H4folate. © 1996 Wiley-Liss, Inc.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
Permalink
