Über die Inhaltsstoffe des grünen Knollenblätterpilzes, XXVI. Die Bausteine des γ‐Amanitins

Wieland, Theodor; Wehrt, Hartmut; Dölling, Jochen

doi:10.1002/jlac.19667000115

Cited by 13 publications

(1 citation statement)

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“…4‐Hydroxyisoleucine was first isolated as a new amino acid lactone from γ‐aminitin hydrolysate1 and later from ϵ‐amanitin,2 one of the cyclic octapeptides found in the highly poisonous mushroom, Amanita phalloides 4. In 1973 Fowden et al3 reported the isolation and identification of free 4‐hydroxyisoleucine from fenugreek seeds, Trigonella foenum graecum L. (Leguminosae).…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of Enantiomerically Pure (2S,3R,4S)‐4‐Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds

et al. 2004

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Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of Enantiomerically Pure (2S,3R,4S)‐4‐Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds

et al. 2004

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Multi‐Step Synthesis and Biological Evaluation of Analogues of Insulin Secretagogue (2S,3R,4S)‐4‐Hydroxyisoleucine

Lajoix¹,

Gross²,

Praly³

2008

Eur J Org Chem

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A series of stereochemically defined analogues of (2S,3R,4S)‐4‐hydroxyisoleucine and related α‐hydroxy acids have been prepared by multi‐step routes from D‐glucose, whereas ketolization between TBDMS‐protected hydroxypropanone and ethyl isocyanoacetate led to racemic analogues. Bioassays showed that of eight newly synthesized compounds, two of them presented an interesting statistical trend to increase glucose‐induced insulin secretion when tested in isolated rat pancreatic islets in the presence of 8.3 mM glucose and at a concentration of 200 μM, which has previously been shown to be effective for (2S,3R,4S)‐4‐hydroxyisoleucine.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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A Practical and Efficient Total Synthesis of Potent Insulinotropic (2S,3R,4S)‐4‐Hydroxyisoleucine through a Chiral N‐Protected γ‐Keto‐α‐aminoester

Marin¹,

Catala²,

Kumar³

et al. 2010

Eur J Org Chem

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(2S,3R,4S)‐4‐Hydroxyisoleucine, which exhibits remarkable insulinotropic activity, is expected to be a potent drug to treat type II diabetes. We propose herein a four‐step synthesis of the enantiopure natural product on the basis of successive Mannich condensation, catalytic epimerization, N‐para‐methoxyphenyl deprotection, and diastereoselective reduction. This compact economical and scalable sequence enables to perfectly control three contiguous chiral centers. It does not involve any chromatographic purification, and the desired compound is obtained in >99 % de, >99 % ee, and 22 % overall yield under our optimized conditions.

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Über die Inhaltsstoffe des grünen Knollenblätterpilzes, XXVI. Die Bausteine des γ‐Amanitins

Cited by 13 publications

References 7 publications

Chemoenzymatic Synthesis of Enantiomerically Pure (2S,3R,4S)‐4‐Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds

Chemoenzymatic Synthesis of Enantiomerically Pure (2S,3R,4S)‐4‐Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds

Multi‐Step Synthesis and Biological Evaluation of Analogues of Insulin Secretagogue (2S,3R,4S)‐4‐Hydroxyisoleucine

A Practical and Efficient Total Synthesis of Potent Insulinotropic (2S,3R,4S)‐4‐Hydroxyisoleucine through a Chiral N‐Protected γ‐Keto‐α‐aminoester

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