162558-25-0Relevant articles and documents
Synthesis and opioid activity of conformationally constrained dynorphin A analogues. 1. Conformational constraint in the 'message' sequence
Arttamangkul,Murray,DeLander,Aldrich
, p. 2410 - 2417 (1995)
A constrained analogue of the opioid peptide dynorphin A (Dyn A) cyclized in the 'message' sequence was designed which may be compatible with the helical conformation proposed by Schwyzer (Biochemistry 1986, 25, 4281-4286) as the conformation Dyn A adopts
Synthesis of the first tricyclic homodetic peptide. Use of coordinated orthogonal deprotection to achieve directed ring closure
Hirschmann, Ralph,Yao, Wenqing,Arison, Byron,Maechler, Laurie,Rosegay, Avery,Sprengeler, Paul A.,Smith III, Amos B.
, p. 7179 - 7202 (1998)
The discovery of somatostatin antagonists at one or more receptor subtypes remains an important goal. We therefore undertook the synthesis of the homodetic tricyclic peptide (1) hoping to cause conformational distortion and thereby achieve this biological goal. The synthetic strategy called for five dimensional orthogonal amino protection. The carboxyl and amino protecting groups were selected to assure the desired selective ring closures. The amino protecting groups were also chosen to permit differentiation between the two lysine ε-amino groups. An improved general cyclization procedure was achieved, which provided the complex c-octapeptide 13 in 93% yield. Biological assay results for 1 are also presented.
NITROGEN CONTAINING BICYCLIC COMPOUNDS AND THEIR USE IN TREATMENT OF BACTERIAL INFECTIONS
-
, (2017/01/23)
Compounds of Formula (I), their preparation, and use in preventing or treating a bacterial infection are disclosed.
Practical and efficient synthesis of orthogonally protected α-2,3-diaminopropionic acid (2,3-Dap), 2,4-diaminobutanoic acid (2,4-Dab), and their N-methylated derivatives
Rao, R. V. Ramana,Tantry, Subramanyam J.,Babu, Vommina V. Suresh
, p. 2901 - 2912 (2007/10/03)
The synthesis of orthogonally protected Fmoc-Dap/Dab (Boc/Z/Alloc)-OH starting from Fmoc-Asp/Glu has been described. The salient features of our synthetic strategy involved formation of Fmoc-Asp/Glu-5-oxazolidinone acids, conversion of acid function to acyl azides, Curtius rearrangement, and hydrolysis of the oxazolidinone group. Copyright Taylor & Francis Group, LLC.
A new approach to the neoglycopeptides: Synthesis of urea- and carbamate-tethered N-acetyl-D-glucosamine amino acid conjugates
Ichikawa, Yoshiyasu,Ohara, Fumiyo,Kotsuki, Hiyoshizo,Nakano, Keiji
, p. 5009 - 5012 (2007/10/03)
(Chemical Equation Presented) A novel approach to the synthesis of Fmoc-protected neoglycopeptide building blocks is described. Oxidation of N-acetyl-D-glucosamine isonitrile afforded the corresponding highly reactive glycopyranosyl isocyanate, which reacted with amino acid derivatives to furnish the corresponding urea- and carbamate-tethered Fmoc-protected N-acetyl-D-glucosamine amino acid conjugates in good yields.
Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent
Akaji, Kenichi,Aimoto, Saburou
, p. 1749 - 1755 (2007/10/03)
The synthesis of MEN11420, a potent tachykinin receptor antagonist, has been achieved. The bicyclic glycosylated structure of MEN11420 was constructed via intramolecular double cyclization using CIP-mediated activation. The head to tail cyclization of the linear precursor, which contained an α-amino acid at its C-terminus, proceeded so rapidly that no serious racemization was apparent at the activated carboxyl function. The desired product was obtained without the need for purification of the intermediates throughout the synthesis.
Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain
Zhang, Zhenyu,Aerschot, Arthur Van,Hendrix, Chris,Busson, Roger,David, Frank,Sandra, Pat,Herdewijn, Piet
, p. 2513 - 2522 (2007/10/03)
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.
Angiopeptin cyclopeptide compounds
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, (2008/06/13)
The invention relates to a compound selected from those of formula (I) (SEQ ID NO:1): STR1 in which R1, R2, X1 and X2 are as defined in the description, useful as inhibitor of the proliferation component of vascular smooth muscle cells.
A new somatostatin analog with optimized ring size inhibits neointima formation induced by balloon injury in rats without altering growth hormone release
Thurieau,Janiak,Krantic,Guyard,Pillon,Kucharczyk,Vilaine,Fauchere
, p. 115 - 122 (2007/10/02)
We report on the synthesis and pharmacological properties of a new series of somatostatin analogs. Two lower homologs of lysine, 2,3-diaminopropanoic acid and 2,4-diaminobutyric acid, were prepared and used for cyclization via amide formation with the side chain of aspartic or glutamic acid in place of natural cystine present in many somatostatin analogs. One resulting compound, although having low binding affinities for somatostatin receptors, displayed a strong potency in inhibiting neointima formation induced by balloon injury in rats at the dose of 100 μg·kg-1·d-1. This dissociation of the antiproliferative effect from the endocrine effect seems to indicate that myointimal growth is not related to a change in growth hormone secretion.
