Synthesis of a pipecolic acid-based bis-amino acid and its assembly into a spiro ladder oligomer

Sharad Gupta; Bhaskar C. Das; Christian E. Schafmeister

doi:10.1021/ol0507672

Synthesis of a pipecolic acid-based bis-amino acid and its assembly into a spiro ladder oligomer

Sharad Gupta
, Bhaskar C. Das
, Christian E. Schafmeister

Pharmaceutical Sciences

University of Pittsburgh

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

23 Scopus citations

Abstract

(Chemical Equation Presented) The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.

Original language	English
Pages (from-to)	2861-2864
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	14
DOIs	https://doi.org/10.1021/ol0507672
State	Published - Jul 7 2005

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abstract = "(Chemical Equation Presented) The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.",

author = "Sharad Gupta and Das, \{Bhaskar C.\} and Schafmeister, \{Christian E.\}",

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AU - Gupta, Sharad

AU - Das, Bhaskar C.

AU - Schafmeister, Christian E.

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Y1 - 2005/7/7

N2 - (Chemical Equation Presented) The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.

AB - (Chemical Equation Presented) The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.

UR - https://www.scopus.com/pages/publications/22244465887

U2 - 10.1021/ol0507672

DO - 10.1021/ol0507672

M3 - Article

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SP - 2861

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis of a pipecolic acid-based bis-amino acid and its assembly into a spiro ladder oligomer

Abstract

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