Synthesis of nonracemic hydroxyglutamic acids

Abstract

Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses of nonracemic hydroxyglutamic acid analogues equipped with functional groups capable for the formation of additional hydrogen bonds, both as donors and acceptors. The majority of synthetic strategies starts from natural products and relies on application of chirons having the required configuration at the carbon atom bonded to nitrogen (e.g., serine, glutamic and pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered.

Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus

“…The second factor is the polar effect that stabilizes a transition state with maximum separation between the nucleophile (Nu – ) and a large group (L). Although the stereoselective synthesis in the Felkin–Anh model has been explored extensively, − to the best of our knowledge, the influence of steric alkyl chain length has not been studied for diastereoselectivity. Here, we investigate the effect of alkyl chain lengths on the diastereoselective synthesis of β-methyl alcohols via the Felkin–Anh model.…”

Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone

“…The structure of hemerocallisamine I (1) features a 4-hydroxyglutamine moiety anchored in a 2-formylpyrrole ring (Figure 1). Both of these subunits are abundant in nature and of synthetic interest [8][9][10]. In addition to hemerocallisamine I (1), several other 4-hydroxyglutamine derivatives, e.g., longitubanine A, oxypinnatanine, and pinnatanine (Figure 1), as well as their N-glycosides, have been isolated directly from H. fulva Molecules 2023, 28, 2177 2 of 15 species [11][12][13].…”