N-substituted glycine

I 7 Versatile Oligo(N-Substituted) Glycines The Many Roles of Peptoids in Drug Discovery Tab. 1.1 Comparison of key characteristics of peptides and peptoids... 

Identity Sequence-specific polymers of amino acids Sequence-specific polymers of N-substituted glycines... 

Specifically, the carboxylates of N -Fmoc-protected (and side chain-protected) N-substituted glycines were activated and then coupled to the secondary amino... 

F. E.Chiral N-substituted glycines can form stable helical conformations. Fold. Design 1997, 2, 369-375. 

R. M.J. Solid-phase syntheses of peptoids using Fmoc-protected N-substituted glycines The synthesis of (retro) peptoids of leu-enkephalin and substance P. Euro. J. Chem. 1998, 4, 1570-1580. 

Bradley and coworkers used the 3D pharmacophore ensemble model to filter a virtual combinatorial library of 3924 N-substituted glycine peptoids (30) containing three known a, actives down to a set of 639 products. Using a cut-down technique, a 160 compound combinatorial library was designed in which the number of compounds that passed the ensemble model filter was maximized. This library contained two of the three known actives present in the original 3924 compound virtual library. This represents a substantial enrichment [(2 actives/160 products) X 100 = 1.25% vs (3 actives/3924 products) x 100 = 0.076%]. 

Zuckermann, R. N., Martin, E. J., Spellmeyer, D. C., et al. (1994) Discovery of nanomolar ligands for 7-transmembrane g-protein-coupled receptors from a diverse n-(substituted)glycine peptoid library../. Med. Chem. 37, 2678-2685. 

Another typical example of 1,3-dipolar addition is the reaction of fullerenes with an azomethine ylide intermediate, which can be readily generated by the reaction of N-substituted glycines or other amino acids with aldehydes or... 

Zuckermann RN, Martin EJ, Spellmeyer DC, Stauber GB, Shoemaker KR, Kerr JM, Figliozzi GM, Goff DA, Siani MA, Simon RJ, Banville SC, Brown EG, Wang L, Richter LS, Moos WH. Discovery of nanomolar ligands for 7-transmembrane G-protein coupled receptors from a diverse N-(substituted)glycine peptoid library. J Med Chem 1994 37 2678-2685. 

One type of oligoamide that can readily be prepared on supports without the need for any partially protected monomers (which are often tedious and expensive to synthesize) are N-substituted oligoglycines (Figure 16.21). These compounds are prepared by a sequence of acylation of a support-bound amine with bromoacetic acid, displacement of the bromide with a primary aliphatic or aromatic amine, and repeated acylation with bromoacetic acid. Because primary amines are cheap and available in large number, this approach enables the cost-efficient production of large, diverse compound libraries. Alternatively, protected N-substituted glycines can also be prepared in solution and then assembled on insoluble supports (Entry 5, Table 16.2). 

Since 1992, workers at Chiron have extended the use of their Zymark robot system from peptide synthesis to libraries containing up to 5000 peptoid [oligo(N-substituted glycines)] [56,91-94] analogues. 

Peptoids are a novel class of non-natural biopolymer based on an N-substituted glycine backbone that are ideally... 

Sanborn TJ, Wu CW, Zuckermann RN, Barron AE. Extreme stabihties of helices formed by water-soluble poly-N-substituted glycines (polypeptoids) with a-chiral side chains. Biopolymers 2002 63 12-20. 

Zuckermann RN. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc. 1992 114 10646-10647. 

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