- Novel μ opioid antagonists derived from the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2)
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Hybrid analogues of the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2, Dmt?=?2′,6′-dimethyltyrosine) containing cis-4-amino-Pro, trans-4-amino-Pro, cis-4-aminoethyl-Pro or cis-4-guanidinylethyl-Pro in the 2 p
- Shi, Saijian,Xu, Jian,Feng, LingLing,Fan, Xin,Chen, Zhen,Qin, Yajuan,Chung, Nga N.,Li, Tingyou,Schiller, Peter W.
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p. 1305 - 1314
(2020/08/05)
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- Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds
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A highly potent CXCR4 antagonist, compound 2, was previously found by using two orthogonal cyclic pentapeptide libraries involving conformation-based and sequence-based libraries based on the pharmacophore of a 14-mer peptidic antagonist, 1. Herein, cyclic tetrapeptides derived from replacements of the dipeptide unit (Nal-Gly) with a γ-amino acid and pseudopeptides cyclized by disulfide and olefin bridges were synthesized to find novel scaffold structures different from that of cyclic pentapeptides. These compounds contain a reduced number of peptide bonds compared to compound 2. Furthermore, several analogues with chemical modification of the side chain of Arg4 in 2 were also prepared. From these, several new leads possessing high to moderate CXCR4-antagonistic activity were characterized.
- Tamamura, Hirokazu,Araki, Takanobu,Ueda, Satoshi,Wang, Zixuan,Oishi, Shinya,Esaka, Ai,Trent, John O.,Nakashima, Hideki,Yamamoto, Naoki,Peiper, Stephen C.,Otaka, Akira,Fujii, Nobutaka
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p. 3280 - 3289
(2007/10/03)
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- Two prolines with a difference: contrasting stereoelectronic effects of 4R/S-aminoproline on triplex stability in collagen peptides [pro(X)-pro(Y)-Gly]n.
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4R/S-Aminoprolines when present in the X-position of collagen peptide [pro(X)-pro(Y)-Gly]n exhibit pH- and stereochemistry-dependent effects on triplex stability.
- Umashankara,Babu, I Ramesh,Ganesh, Krishna N
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p. 2606 - 2607
(2007/10/03)
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- Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain
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Competitive binding of peptides containing basic amino acids to disrupt or prevent the Tat-TAR interaction could result in diminished transcription as well as translation and hence constitutes an alternative way of controlling HIV replication. Therefore, we synthesized guanidinium and amino containing amino acids, based on a proline or an alanine scaffold. The introduction of the guanidinium moiety was best accomplished using 1H- pyrazole-1-carboxamidine hydrochloride, with Pmc used for its protection. The absence of racemization, maintained throughout the whole synthesis, was confirmed by chiral purity determination. These building blocks were smoothly incorporated into oligopeptides, which proved their suitability for use in a combinatorial approach for selecting TAR binding ligands. (C) 2000 Elsevier Science Ltd.
- Zhang, Zhenyu,Aerschot, Arthur Van,Hendrix, Chris,Busson, Roger,David, Frank,Sandra, Pat,Herdewijn, Piet
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p. 2513 - 2522
(2007/10/03)
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