Structural determinants of substrates and inhibitors: Probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate

C. Sean Esslinger; Hans P. Koch; Michael P. Kavanaugh; Dean P. Philips; A. Richard Chamberlin; Charles M. Thompson; Richard J. Bridges

doi:10.1016/S0960-894X(98)00560-5

Structural determinants of substrates and inhibitors: Probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate

C. Sean Esslinger
, Hans P. Koch
, Michael P. Kavanaugh
, Dean P. Philips
, A. Richard Chamberlin
, Charles M. Thompson
, Richard J. Bridges

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

45 Scopus citations

Abstract

Using an intramolecular [2+2] photocyclization, 2,4-methanopyrrolidine- 2,4-dicarboxylate was prepared as a conformationally locked analogue of glutamate. This compound, in combination with two other pyrrolidine dicarboxylates, has been used to define the structural elements that differentiate substrate and nonsubstrate inhibitors of a high-affinity, sodium-dependent glutamate transporter.

Original language	English
Pages (from-to)	3101-3106
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	8
Issue number	21
DOIs	https://doi.org/10.1016/S0960-894X(98)00560-5
State	Published - Nov 1998

Funding

Aelmowledgmeats: This work was funded in part by the NiH: NS27600 (ARC), NS30570 (RJB), and NS33270 (MPK). Support was also provided through an NSF instrument grant (CHE 9302468) for the purchase of the 400 MHz NMR used in this study. CSE was a postdoeto~ fellow of The American Heart Association (9604520S). References and Notes

Funder number
CHE 9302468
R01NS027600

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10.1016/S0960-894X(98)00560-5

Cite this

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title = "Structural determinants of substrates and inhibitors: Probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate",

abstract = "Using an intramolecular [2+2] photocyclization, 2,4-methanopyrrolidine- 2,4-dicarboxylate was prepared as a conformationally locked analogue of glutamate. This compound, in combination with two other pyrrolidine dicarboxylates, has been used to define the structural elements that differentiate substrate and nonsubstrate inhibitors of a high-affinity, sodium-dependent glutamate transporter.",

author = "Esslinger, \{C. Sean\} and Koch, \{Hans P.\} and Kavanaugh, \{Michael P.\} and Philips, \{Dean P.\} and Chamberlin, \{A. Richard\} and Thompson, \{Charles M.\} and Bridges, \{Richard J.\}",

note = "Funding Information: Aelmowledgmeats: This work was funded in part by the NiH: NS27600 (ARC), NS30570 (RJB), and NS33270 (MPK). Support was also provided through an NSF instrument grant (CHE 9302468) for the purchase of the 400 MHz NMR used in this study. CSE was a postdoeto\textasciitilde{} fellow of The American Heart Association (9604520S). References and Notes",

year = "1998",

month = nov,

doi = "10.1016/S0960-894X(98)00560-5",

language = "English",

volume = "8",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T2 - Probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate

AU - Esslinger, C. Sean

AU - Koch, Hans P.

AU - Kavanaugh, Michael P.

AU - Philips, Dean P.

AU - Chamberlin, A. Richard

AU - Thompson, Charles M.

AU - Bridges, Richard J.

N1 - Funding Information: Aelmowledgmeats: This work was funded in part by the NiH: NS27600 (ARC), NS30570 (RJB), and NS33270 (MPK). Support was also provided through an NSF instrument grant (CHE 9302468) for the purchase of the 400 MHz NMR used in this study. CSE was a postdoeto~ fellow of The American Heart Association (9604520S). References and Notes

PY - 1998/11

Y1 - 1998/11

N2 - Using an intramolecular [2+2] photocyclization, 2,4-methanopyrrolidine- 2,4-dicarboxylate was prepared as a conformationally locked analogue of glutamate. This compound, in combination with two other pyrrolidine dicarboxylates, has been used to define the structural elements that differentiate substrate and nonsubstrate inhibitors of a high-affinity, sodium-dependent glutamate transporter.

AB - Using an intramolecular [2+2] photocyclization, 2,4-methanopyrrolidine- 2,4-dicarboxylate was prepared as a conformationally locked analogue of glutamate. This compound, in combination with two other pyrrolidine dicarboxylates, has been used to define the structural elements that differentiate substrate and nonsubstrate inhibitors of a high-affinity, sodium-dependent glutamate transporter.

UR - https://www.scopus.com/pages/publications/0005761614

U2 - 10.1016/S0960-894X(98)00560-5

DO - 10.1016/S0960-894X(98)00560-5

M3 - Article

C2 - 9873684

AN - SCOPUS:0005761614

SN - 0960-894X

VL - 8

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 21

ER -

Structural determinants of substrates and inhibitors: Probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate

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