Stereoselective synthesis of functionalized pyroglutamates

Matthew J. Just; Srinivas Tekkam; Mohammad A. Alam; Subash C. Jonnalagadda; Joseph L Johnson; Venkatram R Mereddy

doi:10.1016/j.tetlet.2011.08.029

Stereoselective synthesis of functionalized pyroglutamates

Matthew J. Just, Srinivas Tekkam, Mohammad A. Alam, Subash C. Jonnalagadda, Joseph L Johnson, Venkatram R Mereddy

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Novel stereoselective synthesis of α-methylene-β-substituted pyroglutamates, and α-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of l-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells.

Original language	English (US)
Pages (from-to)	5349-5351
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2011.08.029
State	Published - Oct 12 2011

Bibliographical note

Funding Information:
We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the funding. Partial support for this work was also provided by research grants from the University of Minnesota Academic Health Center Faculty Development Grant (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure.

Keywords

Baylis-Hillman bromides/acetates
Oxazoles
Pyroglutamates (γ-carboxy-γ-lactams)
Substrate controlled alkylation
Threonine

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title = "Stereoselective synthesis of functionalized pyroglutamates",

abstract = "Novel stereoselective synthesis of α-methylene-β-substituted pyroglutamates, and α-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of l-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells.",

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note = "Funding Information: We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the funding. Partial support for this work was also provided by research grants from the University of Minnesota Academic Health Center Faculty Development Grant (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure. ",

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AU - Just, Matthew J.

AU - Tekkam, Srinivas

AU - Alam, Mohammad A.

AU - Jonnalagadda, Subash C.

AU - Johnson, Joseph L

AU - Mereddy, Venkatram R

N1 - Funding Information: We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the funding. Partial support for this work was also provided by research grants from the University of Minnesota Academic Health Center Faculty Development Grant (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure.

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N2 - Novel stereoselective synthesis of α-methylene-β-substituted pyroglutamates, and α-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of l-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells.

AB - Novel stereoselective synthesis of α-methylene-β-substituted pyroglutamates, and α-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of l-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells.

KW - Baylis-Hillman bromides/acetates

KW - Oxazoles

KW - Pyroglutamates (γ-carboxy-γ-lactams)

KW - Substrate controlled alkylation

KW - Threonine

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Stereoselective synthesis of functionalized pyroglutamates

Abstract

Bibliographical note

Keywords

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