32991-17-6Relevant articles and documents
Conformational variability in short acyclic peptides. Stabilization of multiple ss-turn structures in organic solvents
Awasthi, Satish Kumar,Raghothama, Srinivasa Rao,Balaram, Padmanabhan
, p. 2701 - 2706 (1996)
The conformational characteristics of three hexapeptides Boc-Leu-Xxx-Val-Leu-Aib-Val-OMe (Xxx - Ala 1, D-Ala 2, Gly 3; Aib = α-aminoisobutyryl) have been probed in CDCl3 solution by NMR methods using solvent perturbation of chemical shifts and radical broadening of NH resonances to delineate intramolecularly hydrogen bonded NH groups. Nuclear Overhauser effects (NOEs) provide additional information on preferred backbone conformations. The substituent at position 2 acts as a major conformational determinant. While a continuous 310 helical conformation is favoured for the peptide with Xxx = Ala, a multiple ss-turns conformation is supported by both NMR and CD data for the peptide with Xxx = D-Ala. In the peptide with Xxx = Gly CD and NMR data suggest that both 310 helical and multiple turns conformations are simultaneously populated. The results suggest that incorporation of D-amino acids and Aib residues into all L-sequences may prove useful in generating sequences containing multiple turns.
Metal- and Base-Free Room-Temperature Amination of Organoboronic Acids with N-Alkyl Hydroxylamines
Sun, Hong-Bao,Gong, Liang,Tian, Yu-Biao,Wu, Jin-Gui,Zhang, Xia,Liu, Jie,Fu, Zhengyan,Niu, Dawen
supporting information, p. 9456 - 9460 (2018/07/29)
We have found that readily available N-alkyl hydroxylamines are effective reagents for the amination of organoboronic acids in the presence of trichloroacetonitrile. This amination reaction proceeds rapidly at room temperature and in the absence of added metal or base, it tolerates a remarkable range of functional groups, and it can be used in the late-stage assembly of two complex units.
Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors
Zhang, Jian,Li, Xiaoyang,Jiang, Yuqi,Feng, Jinhong,Li, Xiaoguang,Zhang, Yingjie,Xu, Wenfang
, p. 3055 - 3064 (2014/05/20)
A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds against SKOV3, HL60 and A549 cells were also investigated. Comparing with the control LY52, compound 12u, with excellent activity both in the enzymatic inhibition assay and cell-based assay, could be used as lead compound for the further development of MMP inhibitors.
Synthesis and antitumor properties of the myelopeptide mp-1
Fonina, L. A.,Belevskaya, R. G.,Efremov, M. A.,Kirilina, E. A.,Az'Muko, A. A.,Treshchalina, E. M.,Sedakova, L. A.
, p. 354 - 359,6 (2020/08/31)
The bone marrow-derived peptide Phe-Leu-Gly-Phe-Pro-Thr (MP-1) has been synthesized by the classical methods of peptide chemistry in solution, and its antitumor properties have been studied. It has been shown that MP-1 enhances the efficacy of the cytosta
Design, synthesis and primary activity assay of bi- or tri-peptide analogues with the scaffold l-arginine as amino-peptidase N/CD13 inhibitors
Mou, Jiajia,Fang, Hao,Liu, Yingzi,Shang, Luqing,Wang, Qiang,Zhang, Lei,Xu, Wenfang
experimental part, p. 887 - 895 (2010/05/02)
A series of bi- or tri-peptide analogues with the scaffold l-arginine were designed, synthesized and evaluated for their inhibitory activities against amino-peptidase N (APN) and metalloproteinase-2 (MMP-2). The primary activity assay showed that all the compounds exhibited higher inhibitory activities against APN than MMP-2. Within this series, compounds C6 and C7 (IC50 = 4.2 and 4.3 μM) showed comparable APN inhibitory activities with the positive control bestatin (IC50 = 3.8 μM).
Synthetic and cytotoxic and antimicrobial activity studies on annomuricatin B
Dahiya, Rajiv,Maheshwari, Monika,Yadav, Rakesh
scheme or table, p. 237 - 244 (2009/06/17)
The first total synthesis of annomuricatin B (8) is described via coupling of the tripeptide Boc-L-asparaginyl(benzhydryl)-L-alanyl-L-tryptophan-OH and the tetrapeptide L-leucyl-glycyl-L-thryl-L-proline-OMe followed by cyclization of the linear heptapeptide fragment. On pharmacological investigation, it was observed that the cycloheptapeptide 8 displays moderate cytotoxicity against Datton's lymphoma ascites and Ehrlich's ascites carcinoma cell lines with cytotoxic inhibitory concentration (50%) values of 11.6 and 14.1 μM, in addition to potent antidermatophyte activity against Trichophyton mentagrophytes and Microsporum audouinii with a minimum inhibitory concentration of 6 μg mL-1. Moreover, Gram-negative bacteria and Candida albicans were found to be moderately sensitive towards the newly synthesized peptide.
Classical synthesis of and structural studies on a biologically active heptapeptide and a nonapeptide of bovine elastin
Spezzacatena, Caterina,Perri, Tiziana,Guantieri, Valeria,Sandberg, Lawrence B.,Mitts, Thomas F.,Tamburro, Antonio M.
, p. 95 - 103 (2007/10/03)
The synthesis of two elastin sequences incorporating the structural unit X-G-G-X-G (X = A) is described. In particular, the following peptides and polypeptides were synthesized and characterized: TFA-H2+LGAGGAG-OH, TFA-H2+LGAGGAGVL-OH (both of these inducing stimulation of endogenous elastin production in cultured adult human fibroblast), poly(LGAGGAG), and poly(LGAGGAGVL). The synthesis was accomplished in solution by classical procedures, by using the diphenylphosphoryl azide for the polycondensation step, and the mixed anhydride method for the coupling steps. CD, NMR, and FT-IR measurements gave evidence of quasi-extended (PP II) structures as a peculiar structural feature in the heptapeptide, and a tendency towards flexible β-turns in the nonapeptide. Poly(LGAGGAG) showed greater disorder with respect to the "monomer", the molecular conformation being accountable for by unstructured polypeptide chains together with β-turns. The polymer is able to adopt supramolecular structures reminiscent of those found in elastin. Unlike that of the heptapeptide, polycondensation of the nonapeptide did not afford a linear polymer, but only cyclic derivatives. This could well be due to the tendency of the monomeric nonapeptide to adopt folded conformations.
Synthesis of lipidated eNOS peptides by combining enzymatic, noble metal- and acid-mediated protecting group techniques with solid phase peptide synthesis and fragment condensation in solution
Machauer, Rainer,Waldmann, Herbert
, p. 2940 - 2956 (2007/10/03)
Lipid-modified proteins play decisive roles in important biological processes such as signal transduction, organization of the cytoskeleton, and vesicular transport. Lipidated peptides embodying the characteristic partial structures of their parent lipida
Synthesis of the N-terminal N-myristoylated and S-palmitoylated undetrigintapeptide of endothelial NO-synthase
Machauer, Rainer,Waldmann, Herbert
, p. 1449 - 1453 (2007/10/03)
Endothelial NO synthase (eNOS) is a membrane-bound protein involved in signaling from the blood stream to the surrounding smooth muscle cells. The synthesis of its N-myristolyated and doubly S-palmitoylated N-terminus 1, which determines the localization
Peptide Enolates. C-Alkylation of Glycine Residues in Linear Tri-, Tetra-, and Pentapeptides via Dilithium Azadienediolates
Bossler, Hans G.,Seebach, Dieter
, p. 1124 - 1165 (2007/10/02)
The Boc-protected tripeptides Boc-Val-Gly-Leu-OH (1), Boc-Leu-Sar-Leu-OH (2), Boc-Leu-Gly-MeLeu-OH (3), and Boc-Val-BzlGly-Leu-OMe (64), tetrapeptide Boc-Leu-Gly-Pro-Leu-OH (9), and pentapeptides Boc-Val-Leu-Gly-Abu-Ile-OH (4), Boc-Val-Leu-Sar-MeAbu-Ile-O
