Reference of H-Lys(Boc)-OHOn October 30, 2019 ,《Total Synthesis and Stereochemical Assignment of Streptide》 was published in Journal of the American Chemical Society. The article was written by Isley, Nicholas A.; Endo, Yusuke; Wu, Zhi-Chen; Covington, Brett C.; Bushin, Leah B.; Seyedsayamdost, Mohammad R.; Boger, Dale L.. The article contains the following contents:
Streptide is a peptide-derived macrocyclic natural product that has attracted considerable attention since its discovery in 2015. It contains an unprecedented post-translational modification that intramolecularly links the β-carbon (C3) of a residue 2 lysine with the C7 of a residue 6 tryptophan, thereby forming a 20-membered cyclic peptide. Herein, we report the first total synthesis of streptide that confirms the regiochem. of the lysine-tryptophan crosslink and provides an unambiguous assignment of the stereochem. (3R vs 3S) of the lysine-2 C3 center. Both the 3R and the originally assigned 3S lysine diastereomers were independently prepared by total synthesis and it is the former, not the latter, that was found to correlate with the natural product. The approach enlists a powerful Pd(0)-mediated indole annulation for the key macrocyclization of the complex core peptide, utilizes an underdeveloped class of hypervalent iodine(III) aryl substrates in a palladium-catalyzed C-H activation/β-arylation reaction conducted on a lysine derivative, and provides access to material with which the role of streptide and related natural products may be examined The experimental process involved the reaction of H-Lys(Boc)-OH(cas: 2418-95-3Reference of H-Lys(Boc)-OH)
H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. These amino acids may be present in low concentrations and play a vital part as an intermediate in a biosynthetic pathway, e.g., ornithine, homoserine, or cystathionine. In contrast they may act as a major storage form of nitrogen, e.g., canavanine in the seed of Canavalia ensiformis, or may be formed in high amounts in response to an external stress, e.g., γ-aminobutyrate.Reference of H-Lys(Boc)-OH It is possible that some of these nonprotein amino acids may serve as insecticidal or fungicidal agents.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics