Diversity-oriented approach to unusual amino acid derivatives and heterocycles via methyl 2-acetamidoacrylate and its congeners

Kotha, Sambasivarao; Bandarugattu, Venkata Babu; Krishna, Nimita Gopal

doi:10.1016/j.tet.2014.05.056

Cited by 31 publications

(21 citation statements)

References 156 publications

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“…Reported [4 + 2] cycloaddition reactions of methyl 2-acetamidoacrylate ( 2 ) and its congeners with cyclic/acyclic dienes and azadienes occur under conventional heating or microwave irradiation [ 24 ]. Moreover, the use of titanium tetrachloride as Lewis acidic promoter has been reported [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of constrained analogues of tryptophan

Rossi¹,

Pirovano²,

Negrato³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA Lewis acid-catalysed diastereoselective [4 + 2] cycloaddition of vinylindoles and methyl 2-acetamidoacrylate, leading to methyl 3-acetamido-1,2,3,4-tetrahydrocarbazole-3-carboxylate derivatives, is described. Treatment of the obtained cycloadducts under hydrolytic conditions results in the preparation of a small library of compounds bearing the free amino acid function at C-3 and pertaining to the class of constrained tryptophan analogues.

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Section: Introductionmentioning

confidence: 99%

Synthesis of constrained analogues of tryptophan

Rossi¹,

Pirovano²,

Negrato³

et al. 2015

Beilstein J. Org. Chem.

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“…[1d,e] In addition, Dha derivatives have emerged in recent years as noncanonical residues with strong chemical utility in chemical biology research for studies on the structure, dynamics, and function of natural peptides and post-translationally modified proteins. [2] Furthermore, they have been utilized in chemical synthesis as precursors to saturated αand β-amino acids, [3] heterocycles, and natural products. [4] When generated into peptides/proteins by β-elimination of serine-OH or cysteine-SH functional groups, the unique electrophilic properties of Dha, compared with natural nucleophilic residues, enable site-selective and bioorthogonal reactions to be carried out for protein labeling in living systems through the thio- [2e] and aza [2f] -Michael addition of suitable thiol and amine reagents, respectively, as well as by metal-catalyzed arylation reactions.…”

Section: Introductionmentioning

confidence: 99%

Single‐Step Synthesis of Dehydroalanine Derivatives via a Brønsted Acid‐Catalyzed Multicomponent Reaction

et al. 2020

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A single‐step practical synthesis of dehydroalanine (Dha) derivatives from commercially available starting materials is reported. The approach comprises a Brønsted acid‐catalyzed three‐component condensation reaction of pyruvic acid, an alcohol/thiol, and an amide/carbamate. This protocol provided access to several Dha derivatives, including a novel chiral version modified with diverse functional groups, which might be useful for further transformations in the construction of more complex molecules.

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“…Development of new amide bond isosteres, unnatural amino acids, or secondary structure mimetics for incorporation into pseudopeptides or peptidomimetics is an important research area in peptide drug discovery. These developments aim to modulate physiochemical properties of peptides while keeping/enhancing their biological activity as well as selectivity against biological targets.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Sulfonimidamide‐Based Amino Acid Building Blocks with Orthogonal Protecting Groups

et al. 2019

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Herein, we report the synthesis of novel sulfonimidamides (SIAs) based on amino acid building blocks using a one‐pot method from tert‐butyldiphenylsilyl‐protected (TBDPS) sulfonamides, as well as exploration of orthogonal deprotection strategies. Among the several protecting groups investigated, TBDPS showed higher conversion, allowed UV detection and simple diastereomeric separation; in particular in combination with amino acid tert‐butyl esters. Moreover, we applied the present method to synthesize cyclic five‐membered acyl sulfonimidamides in two steps. The described synthesis of SIA‐based amino acid building blocks in combination with the orthogonal protection groups provide access to unnatural amino acid building blocks useful for further incorporation into larger molecules, such as peptide‐based transition‐state analogues and peptidomimetics. The chirality of the SIA group, as well as its additional point of diversity provided by the extra NH group, creates opportunities for the development of unique compound libraries that explore new chemical space, which is of considerable importance for the pharmaceutical and agrochemical industry.

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Diversity-oriented approach to unusual amino acid derivatives and heterocycles via methyl 2-acetamidoacrylate and its congeners

Cited by 31 publications

References 156 publications

Synthesis of constrained analogues of tryptophan

Synthesis of constrained analogues of tryptophan

Single‐Step Synthesis of Dehydroalanine Derivatives via a Brønsted Acid‐Catalyzed Multicomponent Reaction

Synthesis of Sulfonimidamide‐Based Amino Acid Building Blocks with Orthogonal Protecting Groups

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