@article{SchnabelSchnabelBerndt1971, author = {Schnabel, Eugen and Schnabel, Henning and Berndt, Heinz}, title = {Zur selektiven acidolytischen Abspaltbarkeit der tert.-Butyloxycarbonyl-Gruppe}, series = {Justus Liebigs Annalen der Chemie}, volume = {749}, journal = {Justus Liebigs Annalen der Chemie}, number = {1}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1099-0690}, doi = {10.1002/jlac.19717490111}, pages = {90 -- 108}, year = {1971}, abstract = {Die tert.-Butyloxycarbonyl-Gruppe (Boc) l{\"a}ßt sich mittels reiner Trifluoressigs{\"a}ure nicht selektiv neben dem Benzyloxycarbonyl-Rest (Z) abspalten. Das gelingt auch nicht mit L{\"o}sungen von Trifluoressigs{\"a}ure bzw. Chlorwasserstoff in organischen L{\"o}sungsmitteln. Kern-substituierte Z-Gruppen wie Z(pCl), Z(mCl) oder Z(pNO₂) sind zwar stabiler, werden aber von den obengenannten Reagenzien ebenfalls angegriffen bzw. sind nicht mehr acidolytisch abspaltbar. - Mit 70proz. w{\"a}ßriger Trifluoressigs{\"a}ure gelingt die Abspaltung von Boc neben Z dagegen fast selektiv; dabei werden aber Benzylester, besonders Glutamins{\"a}ure-γ-benzylester, teilweise hydrolysiert, w{\"a}hrend Methyl- sowie {\"A}thylester nahezu best{\"a}ndig sind. Die Brauchbarkeit des Abspaltungsverfahrens wird anhand der schrittweise durchgef{\"u}hrten Synthese zweier Heptapeptid-Derivate gezeigt. - {\"A}hnlich spezifisch gelingt die Abspaltung von Boc mit Bortrifluorid-{\"a}therat in Eisessig; Benzylester sind gegen{\"u}ber diesem Reagenz stabiler als gegen w{\"a}ßrige Trifluoressigs{\"a}ure. Das Bortrifluorid-Verfahren eignet sich besonders f{\"u}r die Abspaltung von Boc-Gruppen neben s{\"a}urelabilen Thiol-Schutzgruppen (Tetrahydropyranyl- bzw. Trityl-Rest) sowie neben dem Cyclocystinyl-Rest. Die Leistungsf{\"a}higkeit der Methode wird durch die Synthese zweier Peptid-Derivate mit S-Trityl-Schutzgruppen belegt. Als Nebenreaktion ist die Acetylierung von aliphatischen Hydroxylgruppen m{\"o}glich. Sie l{\"a}ßt sich vermeiden, wenn man die Spaltung in anderen L{\"o}sungsmitteln durchf{\"u}hrt. Die als Modellverbindungen f{\"u}r Stabilit{\"a}tsuntersuchungen verwendeten Nε-acylierten Lysin-Derivate werden mit dem Aminos{\"a}ureanalysator quantitativ neben Lysin bestimmt.}, language = {de} } @article{NokiharaBerndt1978, author = {Nokihara, Kiyoshi and Berndt, Heinz}, title = {Synthesis of hapten-polypeptide conjugates as antigen models for the N-terminal region of the α-2-chain of rabbit skin collagen}, series = {Journal of the Royal Society of Chemistry: Perkin Transactions 1}, volume = {1978}, journal = {Journal of the Royal Society of Chemistry: Perkin Transactions 1}, number = {3}, publisher = {Royal Society of Chemistry}, address = {Cambridge}, issn = {1364-5463}, doi = {10.1039/P19780000260}, pages = {260 -- 263}, year = {1978}, abstract = {Synthesis of derivatives of the peptide sequence L-pyroglutamyl-L-phenylalanyl-L-aspartyl-glycyl-L-lysyl-glycyl-glycyl-glycine as the antigenic determinant representing the N-terminal non-helical region of the α-2-chain of rabbit skin collagen, and conjugation to two different polypeptide carriers, are described.}, language = {en} } @inproceedings{BerndtTurck1984, author = {Berndt, Heinz and Turck, Christoph W.}, title = {Syntheses of defined peptide derivatives by aminolysis of 3-[Nα-benzyloxycarbonyl peptidyloxy] -2-hydroxy-N-methyl-benzamides at elevated temperatures II. Synthesis of the peptide derivatives Z-Ala-X-Gly-N(Et)2, X=Phe, Leu, Val, Ser (But), Glu (OBut)}, series = {Chemistry of peptides and proteins : proceedings of the Fourth USSR-FRG Symposium, T{\"u}bingen, Federal Republic of Germany, June 8 - 12, 1982 / ed. Wolfgang Voelter ... - Vol. 2}, booktitle = {Chemistry of peptides and proteins : proceedings of the Fourth USSR-FRG Symposium, T{\"u}bingen, Federal Republic of Germany, June 8 - 12, 1982 / ed. Wolfgang Voelter ... - Vol. 2}, editor = {Voelter, Wolfgang}, publisher = {de Gruyter}, address = {Berlin [u.a.]}, isbn = {3-11009-580-7}, pages = {97 -- 103}, year = {1984}, language = {en} } @inproceedings{ZahnBerndtFehrenbach1973, author = {Zahn, Helmut and Berndt, Heinz and Fehrenbach, P.}, title = {Synthese cyclischer Cystinpeptide mit Insulin A-und B-Kettensequenzen}, series = {Peptides 1972 : proceedings of the Twelfth European Peptide Symposium, Reinhardsbrunn Castle, German Democratic Republic, September 1972}, booktitle = {Peptides 1972 : proceedings of the Twelfth European Peptide Symposium, Reinhardsbrunn Castle, German Democratic Republic, September 1972}, editor = {Hanson, Horst}, publisher = {North-Holland Publ. [u.a.],}, address = {Amsterdam [u.a.]}, isbn = {0-7204-4132-3}, pages = {101 -- 102}, year = {1973}, language = {de} } @inproceedings{SchnabelBerndt1973, author = {Schnabel, Eberhard and Berndt, Heinz}, title = {Zur selektive Abspaltbarkeit der t-Butyloxycarbonylgruppe}, series = {Peptides 1971 : proceedings of the Eleventh European Peptide Symposium, Vienna, Austria, April 1971}, booktitle = {Peptides 1971 : proceedings of the Eleventh European Peptide Symposium, Vienna, Austria, April 1971}, editor = {Nesvadba, H.}, publisher = {North-Holland Publ. [u.a.]}, address = {Amsterdam [u.a.]}, isbn = {0-7204-4120-X}, pages = {69 -- 70}, year = {1973}, language = {en} } @inproceedings{KroggelBerndt1984, author = {Kroggel, Matthias and Berndt, Heinz}, title = {The 0-hydroxiphenyloxicarbonyl-group a new base labile amine protecting group}, series = {Peptides 1984 : Proceedings of the 18th European Peptide Symposium Djur{\"o}n{\"a}set, Sweden, June 10 - 15, 1984}, booktitle = {Peptides 1984 : Proceedings of the 18th European Peptide Symposium Djur{\"o}n{\"a}set, Sweden, June 10 - 15, 1984}, editor = {Ragnarsson, Ulf}, publisher = {Almquist \& Wiksell}, address = {Stockholm}, isbn = {91-22-00715-6}, pages = {81 -- 83}, year = {1984}, language = {en} } @phdthesis{Berndt1972, author = {Berndt, Heinz}, title = {Zur Synthese der Sequenz 60-84[Ala71, Gly72, Val73] des Schweineproinsulins als monomeres cyclisches Bis-Cystinpeptidderivat}, address = {Aachen}, pages = {115 S.}, year = {1972}, language = {de} } @book{Berndt2014, author = {Berndt, Heinz}, title = {Neue Kondensations-Methoden zur Synthese definierter Peptid-Derivate}, address = {Aachen}, pages = {XII, VI, 207 S. : graph. Darst.}, year = {2014}, language = {de} } @article{NokiharaBerndt1979, author = {Nokihara, Kiyoshi and Berndt, Heinz}, title = {Darstellung von Bis(S-methoxycarbonylthio)-B-Kette des Rinderinsulins}, series = {Hoppe-Seyler's Zeitschrift f{\"u}r physiologische Chemie}, volume = {360}, journal = {Hoppe-Seyler's Zeitschrift f{\"u}r physiologische Chemie}, number = {1}, issn = {1437-4315}, doi = {10.1515/bchm2.1979.360.1.773}, pages = {773 -- 776}, year = {1979}, language = {de} } @article{Berndt1979, author = {Berndt, Heinz}, title = {Synthese der Sequenz 71—86 des Humanproinsulins, III : Synthese {\"u}ber die Fragmente 71—78 und 79—86}, series = {Hoppe-Seyler's Zeitschrift f{\"u}r physiologische Chemie}, volume = {360}, journal = {Hoppe-Seyler's Zeitschrift f{\"u}r physiologische Chemie}, number = {1}, issn = {1437-4315}, doi = {10.1515/bchm2.1979.360.1.765}, pages = {765 -- 772}, year = {1979}, language = {de} }