120980-88-3Relevant articles and documents
Studies of N-Terminal Templates for α-Helix Formation. Synthesis and Conformational Analysis of (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo4,8>tridecane (Ac-Hel1-OH)
Kemp, D. S.,Curran, Timothy P.,Davis, William M.,Boyd, James G.,Muendel, Christopher
, p. 6672 - 6682 (2007/10/02)
A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxycarbonyl)-5(S)-pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo4,8>tridecane.In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond.In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.
(2S,5S,8S,11S)-1-ACETYL-1,4-DIAZA-3-KETO-5-CARBOXY-10-THIA-TRICYCLO-(2.8.04,8)-TRIDECANE, 1 SYNTHESIS OF PROLYL-PROLINE-DERIVED, PEPTIDE-FUNCTIONALIZED TEMPLATES FOR α-HELIX FORMATION
Kemp, D. S.,Curran, Timothy P.
, p. 4931 - 4934 (2007/10/02)
A convergent synthesis is reported for the title compound 1 (X = OH) from L-4-hydroxyproline and (2S,5S)-trans-1-benzyl-2,5-dicarbomethoxypyrrolidine.The peptides αTemp-(L-Ala)n-OMe (n = 1,2,3,4) and αTemp-L-Ala-L-Phe-L-Lys(ε-Boc)-L-Lys(ε-Boc)-NHMe (αTemp
