The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1. / Thorn, Karina; Nielsen, Carsten Uhd; Jakobsen, Palle; Steffansen, Bente; Zercher, Charles K; Begtrup, Mikael.

In: Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 15, 08.2011, p. 4597-4601.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Thorn, K, Nielsen, CU, Jakobsen, P, Steffansen, B, Zercher, CK & Begtrup, M 2011, 'The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1', Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 15, pp. 4597-4601. https://doi.org/10.1016/j.bmcl.2011.05.108

APA

Thorn, K., Nielsen, C. U., Jakobsen, P., Steffansen, B., Zercher, C. K., & Begtrup, M. (2011). The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1. Bioorganic & Medicinal Chemistry Letters, 21(15), 4597-4601. https://doi.org/10.1016/j.bmcl.2011.05.108

Vancouver

Thorn K, Nielsen CU, Jakobsen P, Steffansen B, Zercher CK, Begtrup M. The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1. Bioorganic & Medicinal Chemistry Letters. 2011 Aug;21(15):4597-4601. https://doi.org/10.1016/j.bmcl.2011.05.108

Author

Thorn, Karina ; Nielsen, Carsten Uhd ; Jakobsen, Palle ; Steffansen, Bente ; Zercher, Charles K ; Begtrup, Mikael. / The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1. In: Bioorganic & Medicinal Chemistry Letters. 2011 ; Vol. 21, No. 15. pp. 4597-4601.

Bibtex

@article{3a2f0e8f7bd743f6b907e2dc82ad9778,
title = "The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1",
abstract = "The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-¿[COCH(2)]-Ser(Bz)-X(aa)-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived {\ss}-keto imides were stereoselectively converted to a-substituted ¿-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K(i)-values ",
keywords = "Former Faculty of Pharmaceutical Sciences",
author = "Karina Thorn and Nielsen, {Carsten Uhd} and Palle Jakobsen and Bente Steffansen and Zercher, {Charles K} and Mikael Begtrup",
note = "Keywords: hPEPT1, ketomethylene, peptides, peptidomimetics, TCEA reaction",
year = "2011",
month = aug,
doi = "10.1016/j.bmcl.2011.05.108",
language = "English",
volume = "21",
pages = "4597--4601",
journal = "Bioorganic & Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Pergamon Press",
number = "15",

}

RIS

TY - JOUR

T1 - The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1

AU - Thorn, Karina

AU - Nielsen, Carsten Uhd

AU - Jakobsen, Palle

AU - Steffansen, Bente

AU - Zercher, Charles K

AU - Begtrup, Mikael

N1 - Keywords: hPEPT1, ketomethylene, peptides, peptidomimetics, TCEA reaction

PY - 2011/8

Y1 - 2011/8

N2 - The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-¿[COCH(2)]-Ser(Bz)-X(aa)-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived ß-keto imides were stereoselectively converted to a-substituted ¿-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K(i)-values

AB - The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-¿[COCH(2)]-Ser(Bz)-X(aa)-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived ß-keto imides were stereoselectively converted to a-substituted ¿-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K(i)-values

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1016/j.bmcl.2011.05.108

DO - 10.1016/j.bmcl.2011.05.108

M3 - Journal article

C2 - 21703856

VL - 21

SP - 4597

EP - 4601

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

SN - 0960-894X

IS - 15

ER -

ID: 33687900