167319-89-3Relevant academic research and scientific papers
Synthesis of fully protected (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxy heptanoic acid
Yoshino, Ryo,Tokairin, Yoshinori,Konno, Hiroyuki
supporting information, p. 1604 - 1606 (2017/04/03)
(2R,3R,4S)-4-Amino-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE), a common constituent of biologically active marine peptides, callipeltin A (1) and neamphamide A, was synthesized as its orthogonally protected derivative from L-glutamic acid in 15 steps. Guanidination by the Mitsunobu condition and osmium-catalyzed dihydroxylation of the corresponding Z-olefin were employed as the key steps.
Synthesis and application of an Nδ-acetyl-N δ-hydroxyornithine analog: Identification of novel metal complexes of deferriferrichrysin
Kobayashi, Kazuya,Oishi, Shinya,Kobayashi, Yuka,Ohno, Hiroaki,Tsutsumi, Hiroko,Hata, Yoji,Fujii, Nobutaka
, p. 2651 - 2655 (2012/06/01)
Synthesis of Fmoc-protected Nδ-acetyl-N δ-(tert-butoxy)-l-ornithine has revealed it to be a metal-chelating amino-acid precursor. This protected amino acid was compatible with the preparation of ferrichrome peptides by standard Fmoc-
Promoting peptide α-helix formation with dynamic covalent oxime side-chain cross-links
Haney, Conor M.,Loch, Matthew T.,Horne, W. Seth
supporting information; experimental part, p. 10915 - 10917 (2011/11/06)
Covalent side-chain cross-linking has been shown to be a viable strategy to control peptide folding. We report here that an oxime side-chain linkage can elicit α-helical folds from peptides in aqueous solution. The bio-orthogonal bridge is formed rapidly
Synthesis of a homologous series of side-chain-extended orthogonally protected aminooxy-containing amino acids
Liu, Fa,Thomas, Joshua,Burke Jr., Terrence R.
scheme or table, p. 2432 - 2438 (2009/04/11)
Practical methodology is reported for the synthesis of a homologous series of side-chain-extended amino acids containing aminooxy functionality bearing orthogonal protection suitable for Fmoc peptide synthesis. These reagents may be useful for the preparation of libraries containing fragments joined by peptide linkers. Georg Thieme Verlag Stuttgart.
Design and concise synthesis of fully protected analogues of L-γ-carboxyglutamic acid
Jiang, Sheng,Li, Peng,Lai, Christopher C.,Kelley, James A.,Roller, Peter P.
, p. 7307 - 7314 (2007/10/03)
The design and synthesis of four nonnaturally occurring amino acid analogues of L-γ-carboxyglutamic acid (Gla), appropriately protected for Fmoc-based solid-phase peptide synthesis (SPPS), is described. These amino acids are Bu-Mal 2, BCAH 3, Pen-Mal 4, a
Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions
Feichtinger, Konrad,Sings, Heather L.,Baker, Tracy J.,Matthews, Kenneth,Goodman, Murray
, p. 8432 - 8439 (2007/10/03)
New guanidinylation reagents are reported. These reagents consist of N,N',N''-tri-Boc-guanidine (1) and N,N',N''-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions, to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents N,N'-di-Boc-N''- triflylguanidine (3) and N,N'-di-Cbz-N''-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.
Facile new method for preparation of optically active protected proline
Yamaguchi, Jun-Ichi,Ueki, Masaaki
, p. 621 - 622 (2007/10/03)
Treatment of L-N-protected 2-amino-5-bromopentanoic acid ester, which was prepared from protected L-glutamic acid, with sodium hydride in tetrahydrofuran (THF) proceeded to give the corresponding protected L-proline in high yield. On the other hand, the reaction of 2-aminobutyric acid derivative with sodium hydride gave the 1-aminocyclopropane-1-carboxylic acid derivative.
Preparation of amino- and carboxy-protected L-α-amino-ω-iodocarboxylic acids
Easmon,Heinisch,Holzer,Matuszczak
, p. 367 - 370 (2007/10/02)
The synthesis of L-α-amino-ω-iodobutyric, valeric, and caproic acid esters protected at the amino function by a benzyloxycarbonyl group is reported.
Insecticidal Properties of Some Derivatives of L-Canavanine
Rosenthal, Gerald A.,Dahlman, D. L.,Crooks, Peter A.,Phuket, Supinan Na,Trifonov, L. S.
, p. 2728 - 2734 (2007/10/03)
The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta .While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine.D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production.The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability.Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue. - Keywords: L-Canavanine; D-canavanine; L-homocanavanine; 1-methyl-L-canavanine; 1-ethyl-L-canavanine; Manduca sexta
