108334-65-2Relevant articles and documents
Application of AlMe3-mediated amidation reactions to solution phase peptide synthesis
Martin, Stephen F.,Dwyer, Michael P.,Lynch, Christopher L.
, p. 1517 - 1520 (1998)
A practical modification of the Weinreb amidation protocol employing amino acids as the amine reaction partner has been developed that allows for the facile synthesis of oligopeptides in solution.
Efficient synthesis of unsymmetrically disubstituted ferrocenes: Towards electrochemical dipeptide-Fc-biosensors
Xu, Yiming,Kraatz, Heinz-Bernhard
, p. 2601 - 2603 (2001)
Unsymmetrically disubstituted ferrocenes (1a, 1b), electrochemical dipeptide-Fc-biosensors, were synthesized by a straightforward synthetic method from 1,1′-ferrocenedicarboxylic acid. In addition, an efficient solution synthesis of pentapeptide (2) was reported.
An efficient and cost-effective approach to kahalalide F N-terminal modifications using a nuisance algal bloom of Bryopsis pennata
Wang, Bin,Waters, Amanda L.,Valeriote, Frederick A.,Hamann, Mark T.
, p. 1849 - 1854 (2015)
Background: Kahalalide F (KF) and its isomer iso-kahalalide F (isoKF), both of which can be isolated from the mollusk Elysia rufescens and its diet alga Bryopsis pennata, are potent cytotoxic agents that have advanced through five clinical trials. Due to a short half-life, narrow spectrum of activity, and a modest response in patients, further efforts to modify the molecule are required to address its limitations. In addition, due to the high cost in producing KF analogues using solid phase peptide synthesis (SPPS), a degradation and reconstruction approach was employed using natural KF from a seasonal algal bloom to generate KF analogues. Methods: N-protected KF was carefully hydrolyzed at the amide linkage between L-Thr12 and D-Val13 using dilute HCl. The synthesis of the C-terminal fragment began with the formation of hexanoic succinimide ester, followed by a reaction with dipeptides. The final coupling reaction was performed between the semisynthesized Fmoc-KF hydrolysis product and the C-terminal fragment, followed by the deprotection of the Fmoc group. Results: Six KF analogues with an addition of an amino acid residue on the N-terminal chain, D-Val14-isoKF (2), Val13-Val14-isoKF (3), D-Leu14-isoKF (4), D-Pro14-isoKF (5), D-Phe14-isoKF (6), and 3,4-2F-D-Phe14-isoKF (7) were prepared using semisynthesis at the exposed N-terminal chain. Conclusions: The overall yield of the medication was 45%. This approach is economical, efficient and amendable to large-scale production while eliminated a nuisance algal bloom. General significance: B. pennata blooms are capable of producing KF in good yields. The semisynthesis from the natural product produced N-terminal modifications for the construction of inexpensive semisynthetic KF libraries.
Synthesis, SAR and biological studies of sugar amino acid-based almiramide analogues: N-methylation leads the way
Das, Dipendu,Khan, Hina P. A.,Shivahare, Rahul,Gupta, Suman,Sarkar, Jayanta,Siddiqui, Mohd. Imran,Ampapathi, Ravi Sankar,Chakraborty, Tushar Kanti
, p. 3337 - 3352 (2017/04/21)
Leishmaniasis, caused by the protozoan parasites of the genus Leishmania, is one of the most neglected diseases endemic in many continents posing enormous global health threats and therefore the discovery of new antileishmanial compounds is of utmost urgency. The antileishmanial activities of a library of sugar amino acid-based linear lipopeptide analogues were examined with the aim to identify potential drug candidates to treat visceral leishmaniasis. It was found that among the synthesized analogues, most of the permethylated compounds exhibited more activity in in vitro studies against intra-macrophagic amastigotes than the non-methylated analogues. SAR and NMR studies revealed that introduction of the N-methyl groups inhibited the formation of any turn structure in these molecules, which led to their improved activities.
