TY - JOUR
T1 - The role of deltorphin II phenylalanine residue in binding to the δ opioid receptor
AU - Honda, T.
AU - Shirasu, N.
AU - Chuman, Y.
AU - Okada, K.
AU - Fujita, T.
AU - Nose, T.
AU - Shimohigashi, Y.
PY - 2000/11
Y1 - 2000/11
N2 - Deltorphin II is a peptide ligand specific for the δ opioid receptor. In order to elucidate the role of Phe3 in binding to the δ opioid receptor, we synthesized a series of analogs in which Phe3 was replaced by various amino acids such as Ala, cyclohexylalanine (Cha), fluorophenylalanines, and other alkyl-side chain amino acids (Val, Leu, and norleucine (Nle)). It was found that [Cha3]deltorphin II and [Nle3]deltorphin II retain almost a full receptor binding affinity. The results indicated that the Phe3-phenyl group of deltorphin II can be substituted by the alkyl groups Such as cyclohexyl and propyl in the interaction with the δ receptor.
AB - Deltorphin II is a peptide ligand specific for the δ opioid receptor. In order to elucidate the role of Phe3 in binding to the δ opioid receptor, we synthesized a series of analogs in which Phe3 was replaced by various amino acids such as Ala, cyclohexylalanine (Cha), fluorophenylalanines, and other alkyl-side chain amino acids (Val, Leu, and norleucine (Nle)). It was found that [Cha3]deltorphin II and [Nle3]deltorphin II retain almost a full receptor binding affinity. The results indicated that the Phe3-phenyl group of deltorphin II can be substituted by the alkyl groups Such as cyclohexyl and propyl in the interaction with the δ receptor.
UR - http://www.scopus.com/inward/record.url?scp=0033724766&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033724766&partnerID=8YFLogxK
U2 - 10.1246/bcsj.73.2549
DO - 10.1246/bcsj.73.2549
M3 - Article
AN - SCOPUS:0033724766
SN - 0009-2673
VL - 73
SP - 2549
EP - 2552
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 11
ER -