Z-L-Dap(Boc)-ol
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Z-L-Dap(Boc)-ol

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Category
Amino Alcohol
Catalog number
BAT-002661
CAS number
199005-69-1
Molecular Formula
C16H24N2O5
Molecular Weight
324.37
Z-L-Dap(Boc)-ol
IUPAC Name
benzyl N-[(2S)-1-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propan-2-yl]carbamate
Synonyms
(2S)-(2-benzyloxycarbonylamino-3-hydroxypropyl)carbamic acid tert-butyl ester; N-ALPHA-BENZYLOXYCARBONYL-N-BETA-T-BUTYLOXYCARBONYL-2,3-DIAMINOPROPANOL
Purity
97% (HPLC)
InChI
InChI=1S/C16H24N2O5/c1-16(2,3)23-14(20)17-9-13(10-19)18-15(21)22-11-12-7-5-4-6-8-12/h4-8,13,19H,9-11H2,1-3H3,(H,17,20)(H,18,21)/t13-/m0/s1
InChI Key
ZRYGVUNFLKWGQH-ZDUSSCGKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCC(CO)NC(=O)OCC1=CC=CC=C1
1. 5'-Fluoro-5'-deoxyaristeromycin
Weikuan Li, Xueqiang Yin, Stewart W Schneller Bioorg Med Chem Lett. 2008 Jan 1;18(1):220-2. doi: 10.1016/j.bmcl.2007.10.095. Epub 2007 Oct 30.
5'-Fluoro-5'-deoxyaristeromycin (2) has been prepared via a Mitsunobu coupling of (1S,2S,3R,4S)-2,3-(cyclopentylidenedioxy)-4-fluoromethylcyclopentan-1-ol with N6-bis-boc protected adenine. This procedure is adaptable to preparing a number of 5'-fluoro-5'-deoxycarbocyclic nucleoside analogs with diversity in the heterocyclic base. Antiviral analysis found promising activity for 2 toward measles but no other viruses. No cytotoxicity was observed for 2.
2. The Nonpeptide Agonist MK-5046 Functions As an Allosteric Agonist for the Bombesin Receptor Subtype-3
Irene Ramos-Alvarez, Tatiana Iordanskaia, Samuel A Mantey, Robert T Jensen J Pharmacol Exp Ther. 2022 Aug;382(2):66-78. doi: 10.1124/jpet.121.001033. Epub 2022 May 29.
Allosteric ligands of various G-protein-coupled receptors are being increasingly described and are providing important advances in the development of ligands with novel selectivity and efficacy. These unusual properties allow expanded opportunities for pharmacologic studies and treatment. Unfortunately, no allosteric ligands are yet described for the bombesin receptor family (BnRs), which are proposed to be involved in numerous physiologic/pathophysiological processes in both the central nervous system and peripheral tissues. In this study, we investigate the possibility that the bombesin receptor subtype-3 (BRS-3) specific nonpeptide receptor agonist MK-5046 [(2S)-1,1,1-trifluoro-2-[4-(1H-pyrazol-1-yl)phenyl]-3-(4-[[1-(trifluoromethyl)cyclopropyl]methyl]-1H-imidazol-2-yl)propan-2-ol] functions as a BRS-3 allosteric receptor ligand. We find that in BRS-3 cells, MK-5046 only partially inhibits iodine-125 radionuclide (125I)-Bantag-1 [Boc-Phe-His-4-amino-5-cyclohexyl-2,4,5-trideoxypentonyl-Leu-(3-dimethylamino) benzylamide N-methylammonium trifluoroacetate] binding and that both peptide-1 (a universal BnR-agonist) and MK-5046 activate phospholipase C; however, the specific BRS-3 peptide antagonist Bantag-1 inhibits the action of peptide-1 competitively, whereas for MK-5046 the inhibition is noncompetitive and yields a curvilinear Schild plot. Furthermore, MK-5046 shows other allosteric behaviors, including slowing dissociation of the BRS-3 receptor ligand 125I-Bantag-1, dose-inhibition curves being markedly affected by increasing ligand concentration, and MK-5046 leftward shifting the peptide-1 agonist dose-response curve. Lastly, receptor chimeric studies and site-directed mutagenesis provide evidence that MK-5046 and Bantag-1 have different binding sites determining their receptor high affinity/selectivity. These results provide evidence that MK-5046 is functioning as an allosteric agonist at the BRS-3 receptor, which is the first allosteric ligand described for this family of receptors. SIGNIFICANCE STATEMENT: G-protein-coupled receptor allosteric ligands providing higher selectivity, selective efficacy, and safety that cannot be obtained using usual orthosteric receptor-based strategies are being increasingly described, resulting in enhanced usefulness in exploring receptor function and in treatment. No allosteric ligands exist for any of the mammalian bombesin receptor (BnR) family. Here we provide evidence for the first such example of a BnR allosteric ligand by showing that MK-5046, a nonpeptide agonist for bombesin receptor subtype-3, is functioning as an allosteric agonist.
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