813436-38-3Relevant academic research and scientific papers
Gramicidin S derivatives containing cis- and trans-morpholine amino acids (MAAS) as turn mimetics
Kapoerchan, Varsha V.,Spalburg, Emile,De Neeling, Albert J.,Mars-Groenendijk, Roos H.,Noort, Daan,Otero, Jose M.,Ferraces-Casais, Patricia,Llamas-Saiz, Antonio L.,Van Raaij, Mark J.,Van Doorn, Joop,Van Der Marel, Gijs A.,Overkleeft, Herman S.,Overhand, Mark
supporting information; experimental part, p. 4259 - 4265 (2010/08/20)
The cyclic decapeptide gramicidin S (GS) was used as a model for the evaluation of four turn mimetics. For this purpose, one of the D-Phe-Pro two-residue turn motifs in the rigid cyclic β-hairp0in structure of GS was replaced with morpholine amino acids (MAA 2-5), differing in stereochemistry and length of the side-chain. The conformational properties of the thus obtained GS analogues (6-9) was assessed by using NMR spectroscopy and X-ray crystallography, and correlated with their biological properties (antimicrobial and hemolytic activity). We show that compound 8, containing the dipeptide isostere trans-MAA 4, has an apparent high structural resemblance with GS and that its antibacterial activity against a panel of Gram positive and -negative bacterial strains is better than the derivatives 6, 7 and 9.
Synthesis and application of carbohydrate-derived morpholine amino acids
Grotenbreg, Gijsbert M.,Christina, Alphert E.,Buizert, Annelies E. M.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Overhand, Mark
, p. 8331 - 8339 (2007/10/03)
The synthesis of series of diversely functionalized ε-morpholine amino acids (MAAs, 5a-h) starting from an ε-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme
