177657-03-3Relevant academic research and scientific papers
An efficient method for the preparation of peptide alcohols
Katritzky, Alan Roy,Abo-Dya, Nader Elmaghwry,Tala, Srinivasa Rao,Gyanda, Kapil,Abdel-Samii, Zakaria Kamel
supporting information; experimental part, p. 4444 - 4447 (2009/12/25)
N-Protected ll-dipeptide alcohols 3a-p, diastereomeric mixture (3d + 3d′) and tripeptide alcohols 6a-c were synthesized by treatment of various amino alcohols with N-protected(α-aminoacyl)benzotriazoles 1a-c, 1f-m, (1a + 1a′) and N-protected(α-dipeptidoyl)benzotriazoles 5a, 5b respectively in good yields with complete retention of chirality.
Lipopeptaibol metabolites of tolypocladium geodes: Total synthesis, preferred conformation, and membrane activity
Rainaldi, Mario,Moretto, Alessandro,Peggion, Cristina,Formaggio, Fernando,Mammi, Stefano,Peggion, Evaristo,Galvez, Jose Antonio,Diaz-de-Villegas, Maria Dolores,Cativiela, Carlos,Toniolo, Claudio
, p. 3567 - 3576 (2007/10/03)
We have synthesized by solution methods and characterized the lipopeptaibol metabolite LP237-F8 extracted from the fungus Tolypocladium geodes and five selected analogues with the Etn → Aib or Etn → Nva replacement at position 8 and/or a triple Gln → Glu(OMe) replacement at positions 5, 6, and 9 (Etn = Cα-ethylnorvaline, Aib = α-aminoisobutyric acid, Nva = norvaline). Conformation analysis, performed by FT-IR absorption, NMR, and CD techniques, strongly supports the view that the six terminally blocked decapeptides are highly helical in solution. Helix topology and amphiphilic character are responsible for their remarkable membrane activity. At position 8 the combination of high hydrophobicity and Ca tetrasubstitution, as in the Etn-containing LP237-F8 metabolite, has a positive effect on membrane interaction.
Synthesis and stereoselective C-C bond-forming reactions of peptide aldehydes
Reetz, Manfred T.,Griebenow, Nils
, p. 335 - 348 (2007/10/03)
The reaction of the activated form of N-protected amino acids 6 and 10 or peptides 14 and 18 with chiral amino alcohols derived from the corresponding α-amino acids affords peptide alcohols which can be oxidized under Swern conditions to produce the corresponding peptide aldehydes 9, 12, 16 and 20. The rational synthesis of diastereomeric di- and tripeptide aldehydes, e.g., (S,S)- or (R,S)-dipeptides as well as (S,S,S)- or (R,S,S)-tripeptides is possible by proper choice of the respective building blocks [(S)- versus (R)-amino acids]. The compounds can be prepared without any undesired α-epimerization. However, the long-term configurational stability depends upon the configuration at the remote stereogenic center, e.g., (R,S)-dipeptide aldehydes epimerize faster than the (S,S) diastereomers. Di- and tripeptide aldehydes 9, 12, 16 and 20 undergo chelation-controlled Grignardtype additions with Me2CuLi that involve little or no undesired α-epimerization. The (S,S)- and (R,S)-dipeptide aldehydes 9 and 12 undergo chelation-controlled pinacol reactions induced by the low-valent vanadium reagent [V2Cl3(THF)6]2[Zn2Cl 6]. The major products in both cases are the corresponding C2-symmetric diols 33 and 36, respectively, which are of interest as potential HIV-protease inhibitors. The degree of stereoselectivity is significantly higher in the case of the (S,S)-dipeptide aldehydes relative to the (R,S) analogs, an observation which can be explained on the basis of three-point binding of the peptides to vanadium. VCH Verlagsgesellschaft mbH, 1996.
