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

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

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.08.029

Cite this

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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.",

author = "Just, \{Matthew J.\} and Srinivas Tekkam and Alam, \{Mohammad A.\} and Jonnalagadda, \{Subash C.\} and Johnson, \{Joseph L.\} and Mereddy, \{Venkatram R.\}",

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. Copyright: Copyright 2011 Elsevier B.V., All rights reserved.",

year = "2011",

month = oct,

day = "12",

doi = "10.1016/j.tetlet.2011.08.029",

language = "English (US)",

volume = "52",

pages = "5349--5351",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Stereoselective synthesis of functionalized pyroglutamates

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. Copyright: Copyright 2011 Elsevier B.V., All rights reserved.

PY - 2011/10/12

Y1 - 2011/10/12

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.

UR - https://www.scopus.com/pages/publications/80052601597

UR - https://www.scopus.com/pages/publications/80052601597#tab=citedBy

U2 - 10.1016/j.tetlet.2011.08.029

DO - 10.1016/j.tetlet.2011.08.029

M3 - Article

AN - SCOPUS:80052601597

SN - 0040-4039

VL - 52

SP - 5349

EP - 5351

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

Stereoselective synthesis of functionalized pyroglutamates

Abstract

All Science Journal Classification (ASJC) codes

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