New approaches to the asymmetric synthesis of α-methylphenylalanine

Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

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“…Alkylation of the resulting oxazinones, followed by deprotection, yielded a,a-disubstituted amino acids. [39] …”

Section: Methodsmentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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“…[1a] In this context, it is important to note that the lack of a low-cost-synthesis of pure samples of AFGPs has been identified as a limiting factor for more extensive studies on AFGPs for commercial and academic applications. [12] Therefore, and within this topic, we have decided to exploit the known peculiarity of certain non-natural Cα-substituted α-amino acids [13] to stabilize helical conformations, [14] particularly α-methylserine (MeSer) and α-methylthreonine (MeThr). Moreover, as we have recently described, [15] these noncoded amino acids show peculiar relative orientations between the carbohydrate moiety and the peptide backbone, which could affect both the formation of hydrophobic pockets and the hydration shell of the glycopeptides.…”

Section: Introductionmentioning

confidence: 99%

Dynamics and Hydration Properties of Small Antifreeze‐Like Glycopeptides Containing Non‐Natural Amino Acids

et al. 2010

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Novel studies on the synthesis and conformation in aqueous solution of three antifreeze‐like glycopeptides containing the sequence Xaa(α‐GalNAc)‐Ala‐Ala, with Xaa being threonine (Thr) or the non‐natural amino acids α‐methylserine (MeSer) or α‐methylthreonine (MeThr), are reported. The study has combined NMR experiments with molecular dynamics simulations. Whereas the Thr derivative is rather rigid in solution and exhibits an extended conformation for the backbone, the non‐natural glycopeptides are fairly flexible and show random coil structures for the peptide sequence. On the other hand, only those glycopeptides with a methyl group at Cβ of the underlying amino acid show perpendicular orientation of the sugar with respect to the peptide moiety. This structural feature, together with the rigidity of the Thr‐containing glycopeptide, makes this system unique to structure the water molecules of its first hydration shell. In addition, despite its chemical similarity, the different observed conformational behaviors of all these molecules, as well as the differences in their dynamics and hydration properties, make them suitable systems to shed light on the key factors that govern antifreeze activity.

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“…Conformationally constrained amino acids [1] are of great interest owing to their dominant role in both synthetic and medicinal chemistry. Incorporation of constrained cyclic amino acids into peptides or peptidomimetics induces conformational restriction and produces significant structural effects that can be used for structural and biomechanistic investigations.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Diels–Alder Cycloaddition of 1‐Aminocyclohexadiene to Chiral Acrylate: Synthesis of Enantiopure Bridgehead‐Aminobicyclo[2.2.2]octane‐2‐carboxylic Acid Derivatives

Songis¹,

Didierjean²,

Laurent³

et al. 2007

Eur J Org Chem

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The acrylate derivative of the (R)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid benzyl ester (R)-2 reacted with 1-(benzyloxycarbonylamino)cyclohexadiene 3 under microwave irradation in solvent-free conditions to yield [4+2] cycloadducts in good yields (91 %). The reaction proceeded with moderate endo selectivity (67 %) and good facial selectivity (90 %). The major cycloadducts were isolated and transformed to afford three enantiopure bicyclic β-amino acids: (1S,2R,4R)-1-(benzyloxycarbonylamino)bicyclo[2.2.2]oct-

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New approaches to the asymmetric synthesis of α-methylphenylalanine

Cited by 52 publications

References 22 publications

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Dynamics and Hydration Properties of Small Antifreeze‐Like Glycopeptides Containing Non‐Natural Amino Acids

Asymmetric Diels–Alder Cycloaddition of 1‐Aminocyclohexadiene to Chiral Acrylate: Synthesis of Enantiopure Bridgehead‐Aminobicyclo[2.2.2]octane‐2‐carboxylic Acid Derivatives

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