Abstract
The asymmetric synthesis of (S)-Boc-N-methyl-p-benzoyl-phenylalanine was performed by alkylation of sultam Boc-sarcosinate. The levorotatory sultam led to (S)-Boc-N-methyl amino acids with high optical purity. This photoreactive amino acid was incorporated into the sequence of a Substance P peptide antagonist. Comparison of the affinity and antagonistic properties of Biotinyl-apa-[D-Pro9, MePhe(pBz)10, Trp11]SP for human tachykinin NK-1 receptor demonstrated that this photoreactive antagonist should be a suitable tool for photolabelling studies.
MeSH terms
-
Alkylation
-
Animals
-
Biotin / analogs & derivatives
-
Biotin / chemical synthesis
-
Biotin / chemistry
-
Biotin / pharmacology
-
CHO Cells
-
Cricetinae
-
Cyclic AMP / metabolism
-
Humans
-
Molecular Conformation
-
Neurokinin-1 Receptor Antagonists
-
Phenylalanine / chemical synthesis*
-
Photochemistry
-
Receptors, Neurokinin-2 / metabolism
-
Structure-Activity Relationship
-
Substance P / analogs & derivatives
-
Substance P / antagonists & inhibitors*
-
Substance P / chemical synthesis
-
Substance P / chemistry
-
Substance P / pharmacology
Substances
-
N-(tert-butoxycarbonyl)-N-methyl-4-benzoylphenylalanine
-
Neurokinin-1 Receptor Antagonists
-
Receptors, Neurokinin-2
-
substance P, biotinyl-apa-Pro(9)-MePhe(pBz)(10)-Trp(11)-
-
Substance P
-
Phenylalanine
-
Biotin
-
Cyclic AMP