804564-31-6Relevant articles and documents
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 (2004)
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
A practical synthesis of gramicidin S and sugar amino acid containing analogues
Grotenbreg, Gijsbert M.,Kronemeijer, Martijn,Timmer, Mattie S. M.,El Oualid, Farid,Van Well, Renate M.,Verdoes, Martijn,Spalburg, Emile,Van Hooft, Peter A. V.,De Neeling, Albert J.,Noort, Daan,Van Boom, Jacques H.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Overhand, Mark
, p. 7851 - 7859 (2007/10/03)
A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a-h) having nonproteinogenic sugar amino acid residues (4-7) incorporated in the turn regions.