222725-35-1Relevant academic research and scientific papers
Cross-metathesis of N-alkenyl peptoids with O- or C-allyl glycosides
Hu, Yun-Jin,Roy, Rene
, p. 3305 - 3308 (1999)
Cross-metathesis of several N-alkenyl-containing oligoglycines derivatives (peptoids) with protected O or C-allyl glycosides of N- acetylglucosamine, galactose, and mannose using Grubbs' ruthenium benzylidene catalyst (Cy3P)2Cl2Ru=CHPh (1) has been achieved in 40 to 52% yields.
An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes
Lin, Yutong,Malins, Lara R.,Malins, Lara R.
supporting information, p. 11811 - 11819 (2021/08/16)
Designer C-terminal peptide amides are accessed in an efficient and epimerization-free approach by pairing an electrochemical oxidative decarboxylation with a tandem hydrolysis/reduction pathway. Resembling Nature's dual enzymatic approach to bioactive primary α-amides, this method delivers secondary and tertiary amides bearing high-value functional motifs, including isotope labels and handles for bioconjugation. The protocol leverages the inherent reactivity of C-terminal carboxylates, is compatible with the vast majority of proteinogenic functional groups, and proceeds in the absence of epimerization, thus addressing major limitations associated with conventional coupling-based approaches. The utility of the method is exemplified through the synthesis of natural product acidiphilamide A via a key diastereoselective reduction, as well as bioactive peptides and associated analogues, including an anti-HIV lead peptide and blockbuster cancer therapeutic leuprolide.
Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion
Lawer, Aggie,Epton, Ryan G.,Stephens, Thomas C.,Palate, Kleopas Y.,Lodi, Mahendar,Marotte, Emilie,Lamb, Katie J.,Sangha, Jade K.,Lynam, Jason M.,Unsworth, William P.
, p. 12674 - 12683 (2020/09/17)
The outcome of ring-expansion reactions based on amino/hydroxyacid side-chain insertion is strongly dependent on ring size. This manuscript, which builds upon our previous work on Successive Ring Expansion (SuRE) methods, details efforts to better define the scope and limitations of these reactions on lactam and β-ketoester ring systems with respect to ring size and additional functionality. The synthetic results provide clear guidelines as to which substrate classes are more likely to be successful and are supported by computational results, using a density functional theory (DFT) approach. Calculating the relative Gibbs free energies of the three isomeric species that are formed reversibly during ring expansion enables the viability of new synthetic reactions to be correctly predicted in most cases. The new synthetic and computational results are expected to support the design of new lactam- and β-ketoester-based ring-expansion reactions.
Application of ring-closing metathesis macrocyclization to the development of Tsg101-binding antagonists
Liu, Fa,Stephen, Andrew G.,Waheed, Abdul A.,Freed, Eric O.,Fisher, Robert J.,Burke Jr., Terrence R.
scheme or table, p. 318 - 321 (2010/04/24)
HIV-1 viral budding involves binding of the viral Gagp6 protein to the ubiquitin E2 variant domain of the human tumor susceptibility gene 101 protein (Tsg101). Recognition of p6 by Tsg101 is mediated in part by a proline-rich motif that contains the sequence 'Pro-Thr-Ala-Pro' ('PTAP'). Using the p6-derived 9-mer sequence 'PEPTAPPEE', we had previously improved peptide binding affinity by employing N-alkylglycine ('peptoid') residues. The current study applies ring-closing metathesis macrocyclization strategies to Tsg101-binding peptide-peptoid hybrids as an approach to stabilize binding conformations and to observe the effects of such macrocyclization on Tsg101-binding affinity and bioavailability.
Synthesis of cyclic dipeptides by ring-closing metathesis
Reichwein, John F.,Liskamp, Rob M. J.
, p. 2335 - 2344 (2007/10/03)
Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by 'amide-to-amide' cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or α,α-dichlorotoluene as an additive.
Fmoc-N-allyl glycine derived N-allyl-2,5-diketopiperazines
Schmidt, Boris,Patzke, Greta R.
, p. 1025 - 1032 (2007/10/03)
The title compound was prepared from chloroacetic acid and elongated to dipeptides which cyclized spontaneously upon Fmoc-deprotection to form N- allylated 2,5-diketopiperazines.
