TY - JOUR
T1 - Synthesis of Partially Modified Retro-Inverso Substance P Analogues and Their Biological Activity
AU - Chorev, Michael
AU - Rubini, Elie
AU - Gilon, Chaim
AU - Wormser, Uri
AU - Selinger, Zvi
PY - 1983/2
Y1 - 1983/2
N2 - Partial retro-inverso modification of a single peptide bond was applied to pGlu-Phe-Phe-Gly-Leu-Met-NH2 (I), a C-terminal hexapeptide analogue of the neuropeptide substance P. Two analogues with reversed peptide bonds, between the pGlu-Phe and Phe-Gly residues, were prepared, purified and characterized. The analogue gpGlu-CRS)-mPhe-Phe-Gly-Leu-Met-NH2 (II) was devoid of either agonistic or antagonistic activity. The second pseu-dopeptide analogue, i.e., pGlu-Phe-gPhe-mGly-Leu-Met-NH2 (III), was found to be a full agonist with 22% of the potency of I in the guinea pig ileum assay.
AB - Partial retro-inverso modification of a single peptide bond was applied to pGlu-Phe-Phe-Gly-Leu-Met-NH2 (I), a C-terminal hexapeptide analogue of the neuropeptide substance P. Two analogues with reversed peptide bonds, between the pGlu-Phe and Phe-Gly residues, were prepared, purified and characterized. The analogue gpGlu-CRS)-mPhe-Phe-Gly-Leu-Met-NH2 (II) was devoid of either agonistic or antagonistic activity. The second pseu-dopeptide analogue, i.e., pGlu-Phe-gPhe-mGly-Leu-Met-NH2 (III), was found to be a full agonist with 22% of the potency of I in the guinea pig ileum assay.
UR - http://www.scopus.com/inward/record.url?scp=0020682790&partnerID=8YFLogxK
U2 - 10.1021/jm00356a003
DO - 10.1021/jm00356a003
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C2 - 6186812
AN - SCOPUS:0020682790
SN - 0022-2623
VL - 26
SP - 129
EP - 135
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 2
ER -