(2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thia-tricyclo -[2.8.04,8]-tridecane, 1 the preferred conformation of 1 (1 ≡ αTemp-OH) and its peptide conjugates αTemp-L-(Ala)n-OR (n=1 to 4) and α-Temp-L-Ala-L-Phe-L-Lys(εBoc)-L-Lys(ε-Boc)-NHMe studies of templates for α-helix formation
✍ Scribed by D.S. Kemp; Timothy P. Curran
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 281 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The conformation of the title compound 1 is deduced from 'H NMR evidence. The stable conformations of u-Temp-(L-Ala) NBMe in MeCN are shown to be distorte 8 -0tBu and a-Temp-L-Ala-L-Phe-L-Lys(cBoc)-L-Lys(&-Boc)ehelices with a bifurcated hydrogen bond.
In the accompanying communication we have reported the synthesis of the helix-inducing template 1 which has been designed to orient the oxygens of three amide carbonyls at the pitch and spacing of a right-handed a-helix. This relatively rigid tricyclic function is expected to act as a nucleation site for a-helix formation when attached at the terminus of a linear polypeptide. In this paper we address the conformations of the template and of peptide-template conjugates.
H-H -ii
The s-cis,s-trans orientations of the 1-acetamido function and two orientations of the methylenethia bridge that links C-8 with C-11 generate the conformations of 1 (X = OMe). An