A Novel Organophosphorus Compound as a Coupling Reagent for Peptide Synthesis

Fan, Chun‐An; Hao, Xiaolin; Ye, Yun‐Hua

doi:10.1080/00397919608003508

Cited by 86 publications

(60 citation statements)

References 4 publications

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“…It was coupled to the lanthionine building block 3 to afford the linear heptapeptide ( Figure 3). After removal of the phenacyl ester (-OPac) from the C-terminus and Boc from N-terminus, the linear peptide was cyclized by a new coupling reagent, 3-(diethoxyphosphoryloxy)-1,2,3-benzotrazin-4(3H)-one (DEPBT) [13], to afford the fully protected heptapeptide 5. Treatment with hydrogen fluoride removed all the protecting groups to yield Lan-7.…”

Section: Design and Synthesismentioning

confidence: 99%

“…The reagents EDC [N-ethyl-N%-(3-dimethylamino propyl)carbodiimide] and BOP [benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate] were purchased from Chem-Impex International (Wood Dale, IL), and HBTU [O-(benzotriazol-1-yl)-N,N,N%,N%-tetramethyluronium hexafluorophosphate] from Applied Biosystem (Foster City, CA). The new coupling reagent, 3-(diethoxyphosphoryloxy)-1,2,3-benzotrazin-4(3H)-one (DEPBT) [13], was a kind gift from Professor Y.H. Ye in Peking University, China.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, conformational analysis and bioactivity of Lan-7, a lanthionine analog of TT-232

Jiang

Howell

et al. 2000

J. Peptide Sci.

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A sandostatin analog, TT-232 (D-Phe-c[Cys-Tyr-D-Trp-Lys-Cys]-Thr-NH2), exhibits strong antitumor effects both in vitro and in vivo. In order to study the structure-activity relationships of TT-232, we designed and synthesized an analog of TT-232, namely Lan-7, in which the disulfide bridge is replaced by a lanthionine monosulfide bridge. Conformational analysis by NMR spectroscopy and computer simulations revealed that Lan-7 and TT-232 adopt very similar conformations in solution, which are quite different from the preferred conformations of sandostatin. Lan-7 has significant growth inhibition effects on a number of human tumor cell lines. It can also induce apoptosis in human ovarian carcinoma 2008 cells. At the same time, Lan-7 produced no toxicity to normal human hematopoietic progenitor cells. All of these results indicate that the modification we made does not alter the anti-tumor activity of TT-232.

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Section: Design and Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, conformational analysis and bioactivity of Lan-7, a lanthionine analog of TT-232

Jiang

Howell

et al. 2000

J. Peptide Sci.

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“…[17] In order to investigate the conditions avoiding the aspartimide derivative 2 in detail, the reaction rate under several coupling conditions was extensively determined. In addition to 2-(1H-9-azobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphonate (HATU), [18] benzotriazole-1-yloxytrispyrrolidinophosphonium hexafluorophosphonate www.chemeurj.org (PyBOP) [19] and 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT), [20] which were used previously, [17] 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU), [21] 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphonate (HBTU) [22] and N,N'-diisopropyl carbodiimide (DIC)/1-hydroxy benzotriazole (HOBt) were chosen as additional coupling reagents. These coupling reagents are commonly used in solid-phase peptide synthesis.…”

Section: Resultsmentioning

confidence: 99%

An Approach for a Synthesis of Asparagine‐Linked Sialylglycopeptides Having Intact and Homogeneous Complex‐Type Undecadisialyloligosaccharides

Yamamoto

Takayanagi

Yoshino

et al. 2006

Chemistry A European J

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This paper describes synthesis of asparagine-linked sialylglycopeptides. The typical feature of our strategy for the synthesis of a sialylglycopeptide is to employ undecadisialyloligosaccharyl Fmoc-asparagine (Fmoc-Asn(CHO)-OH) 1 without protecting groups on its hydroxyl groups except for the benzyl ester of the NeuAc residues. Our synthetic methodology solved the problem of esterification toward sugar hydroxyl groups by activated amino acids during the elongation of a peptide chain. When employing high concentrations of the Fmoc-amino acid, esterification markedly occurred, but the esterification scarcely occurred when employing low concentrations of reactants. Taking advantage of these findings, we examined the synthesis of a high molecular sialylglycopeptide, CTLA-4 fragment (113-150) 13 having two complex-type sialyloligosaccharides by use of native chemical ligation (NCL). As a result, we succeeded in the synthesis of a sialylglycopeptide having a cysteine residue at the N-terminus (CTLA-4: 129-150 fragment) 11 and a sialylglycopeptide-thioester (CTLA-4: 113-128 fragment) 12. Finally, the sialylglycopeptides synthesized were applied to NCL reactions. The reaction successfully afforded the desired product, CTLA-4 (113-150) 13 containing mature and pure complex-type sialyloligosaccharides in excellent purity.

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“…Nach Entfernen der Schutzgruppen an den HyPhe 3 -, HyLeu 4 -und Ser 11 -Seitenketten konnte unter klassischen Bedingungen die konformationsgesteuerte Makrolactamisierung mit einer beachtlichen Ausbeute von 72 % durchgeführt werden. Nach Hydrogenolyse des Z-Carbamats (in Gegenwart von Trifluoressigsäure) wurde Lysobactin (1) erzeugt, wobei sich (wie auch in der gesamten Synthese) die Verwendung von DEPBT (3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4-3H)-on) [27,28] …”

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Totalsynthesen von Lysobactin (Katanosin B)

Campagne

2007

Angewandte Chemie

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Im Wettlauf mit der Natur: Lysobactin (1) ist ein natürliches cyclisches Depsipeptid mit stark antibiotischer Wirkung gegen Vancomycin‐resistente Enterokokken sowie gegen Methicillin‐resistente Stämme von Staphylococcus aureus. Vor kurzem wurden zwei Totalsynthesen von 1 beschrieben, die weitere chemische Modifikationen seiner Struktur und einen tieferen Einblick in den Wirkmechanismus ermöglichen sollten.

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A Novel Organophosphorus Compound as a Coupling Reagent for Peptide Synthesis

Cited by 86 publications

References 4 publications

Synthesis, conformational analysis and bioactivity of Lan-7, a lanthionine analog of TT-232

Synthesis, conformational analysis and bioactivity of Lan-7, a lanthionine analog of TT-232

An Approach for a Synthesis of Asparagine‐Linked Sialylglycopeptides Having Intact and Homogeneous Complex‐Type Undecadisialyloligosaccharides

Totalsynthesen von Lysobactin (Katanosin B)

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