Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, U.S. Gov’t, P.H.S., Journal of Medicinal Chemistry called Stereochemical studies on medicinal agents. 30. Investigation of 4-(3-hydroxyphenyl)-4-methylpipecolic acid as a conformationally restricted mimic of the tyrosyl residue of leucine-enkephalinamide, Author is Sugg, Elizabeth E.; Portoghese, Philip S., which mentions a compound: 10466-61-2, SMILESS is N[C@@H](CC(C)C)C(N)=O.[H]Cl, Molecular C6H15ClN2O, Recommanded Product: H-Leu-NH2.HCl.
The cis and trans forms of enkephalin analog I (R = H) (II) were prepared by coupling the resp. cis and trans forms of pipecolic acid III with H-Gly-Gly-Phe-Leu-NH2 by DCC/HOBt and debenzylating the resulting I (R = CH2Ph) by hydrogenolysis. N-Benzyl-4-piperidinone was treated with m-bromoanisole in the presence of BuLi to give piperidinol IV, which was dehydrated by p-MeC6H4SO3H in refluxing toluene to give tetrahydropyridine V. V was methylated by (MeO)2SO/BuLi to give 4-Me derivative VI, which was treated with HClO4/KCN to give cyanopiperidine VI, which was hydrolyzed by concentrated HCl to give cis- and trans-II. Despite spatial analogy between trans-II and leucine-enkephalinamide, trans-II possessed neither opioid agonist nor antagonist activity.
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