The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1
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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.
I: Bioorganic & Medicinal Chemistry Letters, Bind 21, Nr. 15, 08.2011, s. 4597-4601.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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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