138775-22-1Relevant articles and documents
Total synthesis of proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide
He, Wei,Qiu, Hai-Bo,Chen, Yi-Jie,Xi, Jie,Yao, Zhu-Jun
supporting information, p. 6109 - 6112 (2015/01/09)
Total synthesis of the originally proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide, has been accomplished by using a [(4+1)+3+3]-peptide fragment-coupling strategy and careful examination and optimization
A preparation of N-Fmoc-N-methyl-α-amino acids and N-nosyl-N-methyl-α-amino acids
Di Gioia, Maria Luisa,Leggio, Antonella,Liguori, Angelo,Perri, Francesca,Siciliano, Carlo,Viscomi, Maria Caterina
scheme or table, p. 133 - 143 (2010/08/19)
A convenient route for the synthesis of lipophilic N-Fmoc-N-methyl-α- amino acids and N-nosyl-N-methyl-α-amino acids, interesting building blocks to be used for the preparation of N-methylated peptides, is presented. Both nosyl- and Fmoc-protected monomer
An efficient preparation of N-Methyl-α-amino acids from N-Nosyl-α-amino acid phenacyl esters
Leggio, Antonella,Belsito, Emilia Lucia,De Marco, Rosaria,Liguori, Angelo,Perri, Francesca,Viscomi, Maria Caterina
experimental part, p. 1386 - 1392 (2010/06/11)
Chemical Equation Presented In this paper we describe a simple and efficient solution-phase synthesis of N-methyl-TV-nosyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids. This represents a very important application in peptide synthesis to obtain N-methylated peptides in both solution and solid phase. The developed methodology involves the use of N-nosyl-α-amino acids with the carboxyl function protected as a phenacyl ester and the methylating reagent diazomethane. An important aspect of this synthetic strategy is the possibility to selectively deprotect the carboxyl function or alternatively both amino and carboxyl moieties by using the same reagent with a different molar excess and under mild conditions. Furthermore, the adopted procedure keeps unchanged the acid-sensitive side chain protecting groups used in Fmoc-based synthetic strategies.
Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-α-amino acids
Di Gioia, Maria Luisa,Leggio, Antonella,Liguori, Angelo,Perri, Francesca
, p. 3723 - 3728 (2008/02/05)
(Chemical Equation Presented) We report here a convenient and simple solid-phase synthesis of N-nosyl-N-methyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids, important building blocks for the synthesis of conformationally restricted and protease-resista
Synthesis and characterization of constrained cyclosporin A derivatives containing a pseudo-proline group
Patiny, Luc,Guichou, Jean-Fran?ois,Keller, Michael,Turpin, Olivier,Rückle, Thomas,Lhote, Philippe,Buetler, Timo M.,Ruegg, Urs T.,Wenger, Roland M.,Mutter, Manfred
, p. 5241 - 5249 (2007/10/03)
The chemical synthesis, conformational analysis and receptor binding studies of novel constrained cyclosporin A (CsA) analogues are described. The selective insertion of pseudo-proline (ΨPro) systems featuring different 2-C-substituents at the oxazolidine
Stereocontrol during the formation of 2-C mono-arylated pseudo-prolines by aromatic stacking interaction
Keller, Michael,Lehmann, Christian,Mutter, Manfred
, p. 413 - 422 (2007/10/03)
When treated with anisaldehyde dimethylacetal the O-benzyl ester protected dipeptide Fmoc-NMeIle-Thr-OBzl(2, cf. Scheme 3), cyclizes to the 2- C(S) epimer 3b assigned by NMR spectroscopy to chirality (R) at the 2-C position of the resulting substituted 1,3-oxazolidine (ΨPro) unit, while in the acetalization of the corresponding O-methylester Fmoc-NMeIle-Thr-OMe (6), the 2-C(S) epimer 7a is predominantly formed stereoselectively and in quantitative yield. The course of the reaction can be rationalized by aromatic stacking interactions involving the benzyl ester and aryl ether groups in a transition state close to a product structure of (R) chirality, whereas the lack of such interactions in the case of the methyl ester can be used to direct the acetalization towards the 2-C(S) epimer.
