Design and synthesis of peptide YY analogues with c-terminal backbone amide-to-ester modifications
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Design and synthesis of peptide YY analogues with c-terminal backbone amide-to-ester modifications. / Albertsen, Louise; Andersen, J.J.; Paulsson, J.F.; Thomsen, J.K.; Norrild, Jens Chr.; Strømgaard, K.
In: A C S Medicinal Chemistry Letters, Vol. 4, No. 12, 12.12.2013, p. 1228-1232.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Design and synthesis of peptide YY analogues with c-terminal backbone amide-to-ester modifications
AU - Albertsen, Louise
AU - Andersen, J.J.
AU - Paulsson, J.F.
AU - Thomsen, J.K.
AU - Norrild, Jens Chr.
AU - Strømgaard, K.
PY - 2013/12/12
Y1 - 2013/12/12
N2 - Peptide YY (PYY) is a gut hormone that activates the G protein-coupled neuropeptide Y (NPY) receptors, and because of its appetite reducing actions, it is evaluated as an antiobesity drug candidate. The C-terminal tail of PYY is crucial for activation of the NPY receptors. Here, we describe the design and preparation of a series of PYY(3-36) depsipeptide analogues, in which backbone amide-to-ester modifications were systematically introduced in the C-terminal. Functional NPY receptor assays and circular dichroism revealed that the ψ(CONH) bonds at positions 30-31 and 33-34 are particularly important for receptor interaction and that the latter is implicated in Y receptor selectivity.
AB - Peptide YY (PYY) is a gut hormone that activates the G protein-coupled neuropeptide Y (NPY) receptors, and because of its appetite reducing actions, it is evaluated as an antiobesity drug candidate. The C-terminal tail of PYY is crucial for activation of the NPY receptors. Here, we describe the design and preparation of a series of PYY(3-36) depsipeptide analogues, in which backbone amide-to-ester modifications were systematically introduced in the C-terminal. Functional NPY receptor assays and circular dichroism revealed that the ψ(CONH) bonds at positions 30-31 and 33-34 are particularly important for receptor interaction and that the latter is implicated in Y receptor selectivity.
UR - http://www.scopus.com/inward/record.url?scp=84890450993&partnerID=8YFLogxK
U2 - 10.1021/ml400335g
DO - 10.1021/ml400335g
M3 - Journal article
AN - SCOPUS:84890450993
VL - 4
SP - 1228
EP - 1232
JO - ACS Medicinal Chemistry Letters
JF - ACS Medicinal Chemistry Letters
SN - 1948-5875
IS - 12
ER -
ID: 96081753