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Synthesis of (6S)-5-formyltetrahydropteroyl-polyglutamates and interconversion to other reduced pteroylpolyglutamate derivatives.
Anal Biochem. 1992 Apr; 202(1):82-8.AB

Abstract

5-Formyltetrahydropteroylpolyglutamates can be synthesized and purified directly from dihydropteroylpolyglutamates in a single-step procedure without purification of intermediates and with yields greater than 90%. The procedure involves a coupled enzymatic synthesis of 10-formyltetrahydropteroylpolyglutamates using the enzymes dihydrofolate reductase, serine hydroxymethyltransferase, and C1-tetrahydrofolate synthase with catalytic amounts of NADPH. The 10-formyltetrahydropteroylpolyglutamates are subsequently converted to 5-formyltetrahydropteroylpolyglutamates at 90 degrees C with near quantitative yields. 5-Formyltetrahydropteroylpolyglutamates are the only stable reduced derivatives of tetrahydropteroylpolyglutamates and can be purified and stored indefinitely without decomposition. Additionally, 5-formyltetrahydropteroylpolyglutamates can be readily converted to other derivatives of tetrahydropteroylpolyglutamates with yields greater than 95%. Also described is the synthesis of tetrahydropteroylglutamates labeled at C-11 with either 14C or 13C. Rapid purification procedures for serine hydroxymethyltransferase and C1-tetrahydrofolate synthase from frozen rabbit livers are presented.

Authors+Show Affiliations

Department of Biochemistry, Virginia Commonwealth University, Richmond 23298.No affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

1621989

Citation

Stover, P, and V Schirch. "Synthesis of (6S)-5-formyltetrahydropteroyl-polyglutamates and Interconversion to Other Reduced Pteroylpolyglutamate Derivatives." Analytical Biochemistry, vol. 202, no. 1, 1992, pp. 82-8.
Stover P, Schirch V. Synthesis of (6S)-5-formyltetrahydropteroyl-polyglutamates and interconversion to other reduced pteroylpolyglutamate derivatives. Anal Biochem. 1992;202(1):82-8.
Stover, P., & Schirch, V. (1992). Synthesis of (6S)-5-formyltetrahydropteroyl-polyglutamates and interconversion to other reduced pteroylpolyglutamate derivatives. Analytical Biochemistry, 202(1), 82-8.
Stover P, Schirch V. Synthesis of (6S)-5-formyltetrahydropteroyl-polyglutamates and Interconversion to Other Reduced Pteroylpolyglutamate Derivatives. Anal Biochem. 1992;202(1):82-8. PubMed PMID: 1621989.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of (6S)-5-formyltetrahydropteroyl-polyglutamates and interconversion to other reduced pteroylpolyglutamate derivatives. AU - Stover,P, AU - Schirch,V, PY - 1992/4/1/pubmed PY - 1992/4/1/medline PY - 1992/4/1/entrez SP - 82 EP - 8 JF - Analytical biochemistry JO - Anal. Biochem. VL - 202 IS - 1 N2 - 5-Formyltetrahydropteroylpolyglutamates can be synthesized and purified directly from dihydropteroylpolyglutamates in a single-step procedure without purification of intermediates and with yields greater than 90%. The procedure involves a coupled enzymatic synthesis of 10-formyltetrahydropteroylpolyglutamates using the enzymes dihydrofolate reductase, serine hydroxymethyltransferase, and C1-tetrahydrofolate synthase with catalytic amounts of NADPH. The 10-formyltetrahydropteroylpolyglutamates are subsequently converted to 5-formyltetrahydropteroylpolyglutamates at 90 degrees C with near quantitative yields. 5-Formyltetrahydropteroylpolyglutamates are the only stable reduced derivatives of tetrahydropteroylpolyglutamates and can be purified and stored indefinitely without decomposition. Additionally, 5-formyltetrahydropteroylpolyglutamates can be readily converted to other derivatives of tetrahydropteroylpolyglutamates with yields greater than 95%. Also described is the synthesis of tetrahydropteroylglutamates labeled at C-11 with either 14C or 13C. Rapid purification procedures for serine hydroxymethyltransferase and C1-tetrahydrofolate synthase from frozen rabbit livers are presented. SN - 0003-2697 UR - https://www.unboundmedicine.com/medline/citation/1621989/Synthesis_of__6S__5_formyltetrahydropteroyl_polyglutamates_and_interconversion_to_other_reduced_pteroylpolyglutamate_derivatives_ L2 - https://linkinghub.elsevier.com/retrieve/pii/0003-2697(92)90210-X DB - PRIME DP - Unbound Medicine ER -