Dipeptide template

Based on chiral functional monomers such as (15), MICSPs can be prepared using a racemic template. Thus, using racemic A-(3,5-dinitrobenzoyl)-a-methylbenzy-lamine (16) as template, a polymer capable of racemic resolution of the template was obtained [67]. Another chiral monomer based on L-valine (17), was used to prepare MIPS for the separation of dipeptide diastereomers [68]. In these cases the configu-... 

Parke-Davis targeted a template structure with no formal charge replacing the Glu-Glu dipeptide bridging pTyr with lie (pTyr+3), since the X-ray structure of SH2-peptide complexes suggested that the contribution of the two charged... 

Figure 2.11 LC analysis of cystine DCL. Trace A shows the DCL templated with CaM, and trace B shows the blank DCL. The amplified peaks ( ) are dipeptides ce and cc. Reproduced from Reference 23 with permission of Wiley-VCH Verlag GmbH Co. KGaA. Copyright Wiley-VCH Verlag GmbH Co. KGaA.

Cheng, S. Tarby, C. M. Comer, D. D. Williams, J. P. Caporale, L. H. Myers, P. L. Boger, D. L. A Solution-Phase Strategy for the Synthesis of Chemical Libraries Containing Small Organic Molecules A Universal and Dipeptide Mimetic Template, Bioorg. Med. Chem. 1996, 4, 727. 

As a key feature of the TASP approach, the template is designed to direct and reinforce the folding of the covalently attached secondary structure elements in the predetermined tertiary structures (Scheme 1), e.g. a four a-helical bundle. The major purpose of artificial turn-inducing mimics is to constrain, when incorporated at the appropriate location, the peptide chain into a semi-rigid, defined, spatial arrangement. 39 8-(Aminomethyl)-5,6,7,8-tetrahydro-2-naphthoic acid (Amhn) is designed to substitute for the central dipeptide unit of a reverse turn and is prepared in a five-step procedure starting from commercially available 4-phen-ylbutanoic acid 40 (Scheme 3). 

The most common functional templates are those of simple amino compounds 4, amino acids 5, and dipeptides 8 (Scheme 3). The simplest amino templates, the tris(ethylene amine) ammonia types 6, 7, and 9 first used in organic dendrimers, have only just begun to be applied in forming peptide dendrimers. Constrained and usual amino acids and heterocyclic compounds such as porphyrin 13, have also been reported.1691... 

Given these requirements, it is obvious that the P-tetralin based N- and C-caps could not be used as position-independent templates. While the P-tetralin amino acid and the dipeptide units are compatible with a position-independent template design, the biphenyl ether linker unit clearly was not. In N- and C-caps, the linker unit forms a side chain (P-tetralin) to backbone constraint (either to the C-terminal carboxylate or the N-terminal amine), and only one attachment site for a peptide... 

A library of vancomycin analogues has been prepared using ring closing metathesis reactions in aqueous solution (Nicolaou, K. C., Hughes, R., Cho, S. Y., Wissinger, N., Labischinski, H., Endermann, R. Chem. Eur. J. 2001, 7, 3824) a kinetic template effect was observed when the library was prepared in the presence of a dipeptide trap. 

Cheng S, Tarby CM, Comer DD, Williams JP, Caporale LH, Myers PL, Boger DL, A solution-phase strategy for the synthesis of chemical libraries containing small organic molecules A universal and dipeptide mimetics template, Bioorg. Med. Chem., 4 727-737, 1996. 

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