Studies on the Non‐Mevalonate Pathway − Preparation and Properties of Isotope‐Labeled 2 C ‐Methyl‐ D ‐erythritol 2,4‐Cyclodiphosphate | Zendy

Schuhr Christoph A. | Zendy; Hecht Stefan | Zendy; Kis Klaus | Zendy; Eisenreich Wolfgang | Zendy; Wungsintaweekul Juraithip | Zendy; Bacher Adelbert | Zendy; Rohdich Felix | Zendy

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Studies on the Non‐Mevalonate Pathway − Preparation and Properties of Isotope‐Labeled 2 C ‐Methyl‐ D ‐erythritol 2,4‐Cyclodiphosphate

Author(s) -

Schuhr Christoph A.,

Hecht Stefan,

Kis Klaus,

Eisenreich Wolfgang,

Wungsintaweekul Juraithip,

Bacher Adelbert,

Rohdich Felix

Publication year - 2001

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/1099-0690(200109)2001:17<3221::aid-ejoc3221>3.0.co;2-u

Subject(s) - erythritol , chemistry , isotopomers , enzyme , yield (engineering) , biocatalysis , terpenoid , biosynthesis , mevalonate pathway , stereochemistry , catalysis , biochemistry , organic chemistry , reaction mechanism , molecule , materials science , metallurgy

Recent studies have shown that 2 C ‐methyl‐ D ‐erythritol 2,4‐cyclodiphosphate can be formed from 2 C ‐methyl‐ D ‐erythritol 4‐phosphate by the consecutive action of IspD, IspE and IspF proteins in the non‐mevalonate pathway of isoprenoid biosynthesis. We describe here rapid one‐pot strategies for the enzyme‐assisted preparation of this compound from isotope‐labeled pyruvate and glucose that are optimized for the introduction of 13 C or 14 C and afford a wide variety of isotopomers in mmol quantity. The one‐pot reactions involving up to 10 forward reaction steps and up to 15 enzyme catalysts have an overall yield of 50 to 80% of purified product.

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