161,233 research outputs found
Small gold nanoparticles for interfacial Staudinger-Bertozzi ligation
No full textSmall gold nanoparticles (AuNPs) that possess interfacial methyl-2-(diphenylphosphino)benzoate moieties have been successfully synthesized (Staudinger-AuNPs) and characterized by multi-nuclear MR spectroscopy, transmission electron microscopy (TEM), UV-Vis spectroscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy (XPS). In particular, XPS was remarkably sensitive for characterization of the novel nanomaterial, and in furnishing proof of its interfacial reactivity. These Staudinger-AuNPs were found to be stable to the oxidation of the phosphine center. The reaction with benzyl azide in a Staudinger-Bertozzi ligation, as a model system, was investigated using P-31 NMR spectroscopy. This demonstrated that the interfacial reaction was clean and quantitative. To showcase the potential utility of these Staudinger-AuNPs in bioorganic chemistry, a AuNP bioconjugate was prepared by reacting the Staudinger-AuNPs with a novel azide-labeled CRGDK peptide. The CRGDK peptide could be covalently attached to the AuNP efficiently, chemoselectively, and with a high loading
Synthese von Phosphin-, Phosphon- und Phosphoramidaten mittels Staudinger Reaktionen
No full textTable of contents 1 INTRODUCTION: PHOSPHORUS-NITROGEN COMPOUNDS AND THE
STAUDINGER REACTION—A GENERAL SURVEY 1 1.1 The Staudinger reaction and its
mechanism 3 1.2 Reactions of iminophosphoranes, phosphin-, phosphon- and
phosphorimidates 5 1.2.1 Hydrolysis of iminophosphoranes, phosphin-, phosphon-
and phosphorimidates 6 1.2.1.1 Hydrolysis of iminophosphoranes – the
Staudinger reduction and its variants 6 1.2.1.2 Hydrolysis of phosphin-,
phosphon- and phosphorimidates 11 1.2.2 Alkylation of iminophosphoranes,
phosphin-, phosphon- and phosphorimidates 13 1.2.3 The aza-Wittig reaction 14
1.2.4 Rearrangement of phosphazenes 18 1.2.4.1 Thermal and electrophile
catalyzed rearrangement 18 1.2.4.2 Phosphorimidate-amidate rearrangement
catalyzed by Lewis acids 19 1.2.4.3 The 3-aza-2-phospha-1-oxa-Cope
rearrangement 20 1.2.4.4 Synthesis of allenamides by the 3-aza-2-phospha-1
-oxa-Cope rearrangement 28 1.2.5 Staudinger reaction with silylated phosphinic
acid derivatives 30 1.3 Staudinger ligation & traceless Staudinger ligation 31
1.3.1 The Staudinger ligation 33 1.3.2 The traceless Staudinger ligation 34
1.3.3 Application of the Staudinger ligation & the traceless Staudinger
ligation 36 1.3.3.1 Peptide ligation, peptide protein ligation and peptide
cyclization by the traceless Staudinger ligation 36 1.3.3.2 The Staudinger
ligation as method for bioconjugation 37 1.4 Phosphorus-nitrogen compounds in
catalysis 39 1.4.1 Lewis base catalysis 39 1.4.2 Brønsted acid catalysis 43
1.5 Synthesis of phosphonamidates and phosphonamidate peptides via chloridates
and chloridites 45 1.5.1 Synthesis of phosphonamidates from phosphonate mono-
and diesters via phosphonochloridates 46 1.5.1.1 Synthesis of phosphonamidates
from phosphonic acid diesters with phosphorus pentachloride 46 1.5.1.2
Synthesis of phosphonamidates from the phosphonic acid monoester 47 1.5.2
Synthesis of phosphonamidates from P(III)-precursors 48 1.5.3 Atherton-Todd
reaction 49 1.6 Phosphonamidates as protease inhibitors 52 1.6.1 Proteases
–function and classification 52 1.6.2 Protease inhibitors 53 1.6.3
Phosphonamidates as protease inhibitors 56 2 OBJECTIVE 61 3 DISCUSSION 65 3.1
Synthesis of N,N-disubstituted phosphin- and phosphoramidates via a Lewis
acid- or alkyl halide-catalyzed rearrangement 65 3.1.1 Synthesis of
N,N-disubstituted phosphoramidates via a Lewis acid-catalyzed phosphorimidate
rearrangement 69 3.1.2 Lewis Acid or Alkyl Halide Promoted Rearrangements of
Phosphor- and Phosphinimidates to N,N-Disubstituted Phosphor- and
Phosphinamidates 83 3.2 Peptide and Protein Functionalization by the
Staudinger-phosphite and the Staudinger-phosphonite reaction 123 3.2.1
Chemoselective Staudinger-Phosphite Reaction of Azides for the Phosphorylation
of Proteins 127 3.2.2 Staudinger-Phosphonite Reactions for the Chemoselective
Transformation of Azido-Containing Peptides and Proteins 149 3.3 Synthesis of
phosphonamidates and phosphonamidate peptides from aryl azides by the
Staudinger reaction 221 3.3.1 Synthesis of phosphonamidate peptides by
Staudinger reactions of silylated phosphinic acids and esters 223 3.4
Staudinger reaction of silylated phosphinic acid esters with alkyl azides 255
3.4.1 Outline 255 3.4.2 Synthesis of alkyl azido compounds, methyl
phenylphosphinate and monomethyl phenylphosphonate 257 3.4.2.1 Synthesis of
alkyl azido substrates 257 3.4.2.2 Synthesis of azido peptides 257 3.4.2.3
Synthesis of methyl phenylphosphinate and monomethyl phenylphosphonate 259
3.4.3 Analysis of the product mixtures and products 260 3.4.4 Comparison of
methyl (trimethylsilyl) phenylphosphonite and dimethyl phenylphosphonite in
the Staudinger reaction with an azido glycine peptide 260 3.4.5 Staudinger
reaction of methyl (trimethylsilyl) phenylphosphonite with small alkyl azides
262 3.4.5.1 More detailed examination of the Staudinger reaction with dodecyl
azide 266 3.4.5.2 Isolation and structural analysis of products derived from
the Staudinger reaction with 3-phenylpropyl azide 269 3.4.5.3 Mechanistic
investigation by 15N-labeling of 3-phenylpropyl azide 271 3.4.5.4 Solvent
effects 280 3.4.5.5 Temperature effect 283 3.4.5.6 Influence of the silylation
reagent on the Staudinger reaction 284 3.4.6 Staudinger reaction of azido
glycine peptides with methyl phenylphosphinate and a silylation reagent 294
3.4.6.1 Temperature effect 295 3.4.6.2 Influence of the silylation reagent on
the Staudinger reaction 296 3.4.6.3 Reaction of the azido glycine peptide with
methyl phenylphosphinate and BSA in solution 299 3.4.6.4 MS/MS measurements of
the isolated phosphonamidate peptide and the side product 299 3.4.7 Studies on
the Staudinger reaction with 2-azido-2-methyl alanine peptides 300 3.5
Stability studies on phosphonamidates 302 3.5.1 Degradation of methyl
N,P-diphenylphosphonamidate at different TFA-concentrations 303 3.5.2
Degradation of methyl N-benzyl-P-phenylphosphonamidate at different TFA-
concentrations 306 4 CONCLUSION AND OUTLOOK 311 5 EXPERIMENTAL PART 319 5.1
Synthesis of azido compounds 7a,b,h,i 320 5.1.1 Synthesis of dodecyl azide
(7a), 3-phenylpropyl azide (7b) and 15N-labled 3-phenylpropyl azide (15N-7b)
320 5.1.2 Dodecyl azide (7a) 320 5.1.3 3-Phenylpropyl azide (7b) 321 5.1.4
15N-3-Phenylpropyl azide (15N-7b) 321 5.1.5 Synthesis of azido acetic acid
(7h) 321 5.1.6 2-Azido-2-methylpropionic acid (7i) 322 5.2 Synthesis of methyl
phenylphosphinate (182), monomethyl phenylphosphinate (187) and methyl
P-phenylphosphonamidate (195) 323 5.2.1 Synthesis of methyl phenylphosphinate
(182) 323 5.2.2 Synthesis of monomethyl phenylphosphinate (187) 323 5.2.3
Synthesis of methyl P-phenylphosphonamidate (195) 324 5.3 Staudinger reaction
of silylated phosphinic acid esters with dodecyl and 3-phenylpropyl azide 325
5.3.1 General procedure for the Staudinger reaction with silylated phosphinic
acid esters 325 5.3.2 Staudinger reaction with dodecyl azide (7a) 325 5.3.3
Synthesis of methyl P-phenyl-(3-phenylpropyl)phosphonamidate (183b) 326 5.3.4
Synthesis of methyl P-phenyl-14/15N-(3-phenylpropyl)phosphonamidate (15N-183b)
(1:1) 327 5.3.5 Synthesis of (E/Z)-methyl
phenyl(2-(3-phenylpropylidene)hydrazinyl)phosphinate ((E/Z)-192b) 328 5.3.6
Synthesis of 14/15N-(E/Z)-methyl
phenyl(2-(3-phenylpropylidene)hydrazinyl)phosphinate (15N-(E/Z)-192b) (1:1)
329 5.3.7 Dependence of the Staudinger reaction on the solvent, temperature
and silylation reagent 330 5.3.7.2 Solvent effect 332 5.3.7.3 Temperature
effect 335 5.3.7.4 Influence of the silylation reagent on the Staudinger
reaction 336 5.3.8 Staudinger reaction with
1,3-dichloro-1,1,3,3-tetramethyldisiloxane 339 5.4 Peptides synthesis 339
5.4.1 Peptide synthesis on NovaSyn® TG HMBA resin – azido peptides 7c, d, f
339 5.4.1.1 Synthesis of azido glycine peptide 7c 341 5.4.1.2 Synthesis of
azido glycine peptide 7d 341 5.4.1.3 Synthesis of 2-azido-2-methyl alanine
peptide 7f 342 5.4.2 Peptide synthesis on a Gly-preloaded Wang resin – azido
peptides 7e and g 343 5.4.2.1 Synthesis of azido glycine peptide 7e 343
5.4.2.2 Synthesis of 2-azido-2-methyl alanine peptide 7g 344 5.5 Staudinger
reaction with azido peptides 345 5.5.1 Staudinger reaction on solid support –
General procedure 345 5.5.2 Staudinger reaction in solution – General
procedure 345 5.5.3 Staudinger reaction between azido glycine peptide 7c and
dimethyl phenylphosphonite (188) 345 5.5.4 Staudinger reaction between azido
glycine peptide 7c and methyl phenylphosphinate (182) with BSA 346 5.5.5
Staudinger reaction at 4 °C, rt and 30 °C 347 5.5.6 Staudinger reaction with
different silylation reagents 349 5.5.6.1 Staudinger reaction with TBDPCl and
methyl phenylphosphinate (182) 349 5.5.6.2 Staudinger reaction with TMSCl and
methyl phenylphosphinate (182) 351 5.5.6.3 Staudinger reaction with MSTFA or
TBDMSTFA and methyl phenylphosphinate (182) 352 5.5.7 Staudinger reaction in
solution 355 5.5.8 Purification of 183e and (E/Z)-192e for MS/MS analysis 356
5.5.9 Studies on the Staudinger reaction with 2-azido-2-methyl alanine
peptides 7f and 7g 357 5.5.10 Stability studies 359 6 LITERATURE 363 7
CURRICULUM VITAE 373 8 APPENDIX 379 8.1 NMR spectra 379 8.1.1 NMR spectra of
15N-3-phenylpropyl azide (15N-7b) 379 8.1.2 NMR spectra to the Staudinger
reaction between dodecyl azide (7a) and methyl phenylphosphinate (182) (6.eq.)
with BSA (18 eq.) 380 8.1.3 NMR spectra of methyl
P-phenyl-(3-phenylpropyl)phosphonamidate (183b) 383 8.1.4 NMR spectra of
methyl P-phenyl-14/15N-(3-phenyl-propyl)phosphonamidate (15N-183b) 386 8.1.5
NMR spectra of (E/Z)-methyl
phenyl(2-(3-phenylpropylidene)hydrazinyl)phosphinate ((E/Z) 192b) 388 8.1.6
NMR spectra of 14/15N-(E/Z)-methyl
phenyl(2-(3-phenylpropylidene)hydrazinyl)-phosphinate (15N-(E/Z)-192b) 391 8.2
Solvent effect – 31P-NMR and LC spectra (UV-trace) 393 8.3 Temperature effect
– 31P-NMR and LC spectra (UV-trace) 397 8.4 Influence of the silylation
reagent on the Staudinger reaction – 31P-NMR and LC spectra (UV-trace) 400
8.4.1 Silylation with BSA 400 8.4.2 Silylation with MSTFA 403 8.4.3 Silylation
with TMSCl 406 8.4.4 Silylation with TESCl 408 8.4.5 Silylation with TBDMSCl
409 8.4.6 Silylation with MTBSTFA 409 8.4.7 Silylation with TBDSPCl 410 8.4.8
Silylation with TPSCl 412Phosphorus-nitrogen compounds play a decisive role in organic and medicinal
research. Due to their unique properties and biological activity, they are
applied as catalysts in organic transformations or as inhibitors for the
treatment of diverse diseases. The STAUDINGER REACTION developed in 1919 by
Herman Staudinger enables a straightforward entrance to various P-N compounds.
Within this thesis, different variants of the Staudinger reaction were
investigated for the synthesis of phosphin-, phosphon- and phosphoramidates
and their application for peptide and protein modifications. In the first
project, the Staudinger reaction and a following rearrangement was
investigated. By performing the Staudinger reaction between phosphites and
azides under anhydrous conditions, a rearrangement of the resulting
phosphorimidates can be initiated by addition of alkyl halides or Lewis acids
leading to N,N-disubstituted phosphoramidates. Optimization of the reaction
conditions and screening of different Lewis acids showed that heating in
benzene at 80°C and 1 mol% of BF3∙Et2O or TMSOTf are the most effective
reaction conditions for the rearrangement. The Staudinger reaction and the
subsequent rearrangement proceeded in high yields (63-99%) with a variety of
different alkyl, aryl and allyl azides and with trimethyl, triethyl, tributyl
and triallyl phosphite as trivalent phosphorus counterparts. The development
of a one-pot procedure starting from alkyl bromides, mesylates or tosylates
further facilitated the reaction by avoiding isolation of the potentially
explosive azides. Moreover, the alkyl halide- and the Lewis acid-catalyzed
rearrangement reaction could be transferred to phosphinimidates leading to
N,N-disubstituted phosphinamidates in yields between 36% and 83%. In the
second project, the Staudinger reaction and following hydrolysis to phosphon-
and phosphoramidates was probed as method for the bioorthogonal, site-
selective and metal-free functionalization of peptides and proteins.
Preliminary studies of the Staudinger reaction with benzyl or phenyl azide and
unprotected azido peptides with different phosphites and phosphonites could
prove its applicability at room temperature in an aqueous environment as well
as its bioorthogonality. All reactions led to high yields and a clean
conversion of the azides to the desired phosphon- and phosphoramidates.
Finally, the Staudinger-phosphite and the Staudinger-phosphonite reaction
could be used for the functionalization of azido proteins, i.e. for PEGylation
or chemical phosphorylation. In the third project, the Staudinger reaction
between silylated phosphinic acids and azides was applied to the synthesis of
phosphonamidates and phosphonamidate peptides. The treatment of phosphinic
acids or their esters with a silylation reagent, like
bis(trimethylsilyl)acetamide, under argon atmosphere generated silyl
phosphonites, which could be reacted in situ with different aryl azides.
Afterwards, desilylation was achieved with TBAF, HF∙pyridine or sodium
hydroxide solution. In all cases the desired phosphonamidates were obtained in
moderate to excellent yields (30-95%). Furthermore, the described reaction
procedure enabled the conversion of unprotected azido peptides containing a
N-terminal para-azidobenzoic acid on solid support. The reaction on solid
support allowed easy removal of reagents and simultaneous TMS-deprotection and
cleavage from the resin under basic conditions (NaOH/1,4-dioxane). The
phosphonamidates peptides were obtained in high conversions and purity. It has
to be noted that the excess of silylation reagent leads to protection of the
functional groups during the reaction. When alkyl azides were used in the
Staudinger reaction with silylated phosphinic acids, the reaction led to the
formation of by-products. Especially if azido glycine peptides were employed
in the reaction, the desired phosphonamidate was only formed in small amounts.
Based on a more detailed exploration of the formed by-products, of the
influence of different reaction conditions on the reaction and 15N-labeling
experiments, a mechanism for the side reaction was proposed. The proposed
mechanism of the side reaction is initiated by the decomposition of the
phosphazide leading to the formation of methyl P-phenylphosphonamidate and a
diazo compound. The diazo compound then further reacts with the silyl
phosphonite under formation of the observed by-product with a
P(O)-NH-N=C-moiety.Phosphor-Stickstoff-Verbindungen spielen in der organischen und medizinischen
Chemie eine wichtige Rolle und finden beispielsweise Einsatz als Katalysatoren
oder Inhibitoren. Die 1919 von Herman Staudinger entwickelte STAUDINGER
REAKTION ermöglicht, einen Zugang zu P-N-Verbindungen und wurde im Rahmen
dieser Arbeit näher untersucht. Das erste Projekt dieser Arbeit bestand in der
Untersuchung der Staudinger-Reaktion und einer nachfolgenden Lewis-Säure- oder
Alkylhalogenid-katalysierten Umlagerung. Ausgehend von den über die Staudinger
Reaktion hergestellten Phosphin- und Phosphorimidaten kann unter wasserfreien
Bedingungen eine Umlagerung zu den entsprechenden N,N-disubstituierten
Amidaten eingeleitet werden. Im Rahmen der Doktorarbeit wurden verschiedene
Lewis-Säuren hinsichtlich ihrer Fähigkeit, eine solche Umlagerung von
Phosphorimidaten zu initiieren, untersucht. BF3∙EtO und TMSOTf erwiesen sich
als die geeignetsten Katalysatoren. Um die Anwendungsbreite der Reaktion zu
untersuchen, wurden unterschiedliche organische Azidverbindungen hergestellt
und verwendet. Dabei lieferten sowohl primäre, sekundäre und tertiäre
alkylische als auch arylische Azide die entsprechenden Phosphoramidate in
guten bis sehr guten Ausbeuten zwischen 63-99 %. Außerdem war es möglich, auch
die trivalenten Phosphorverbindungen zu variieren, und Methyl-, Ethyl-, Butyl-
und Allylgruppen konnten erfolgreich umgelagert werden. Um die optimierte
Umsetzung weiter zu vereinfachen und die Isolierung von potenziell explosiven
Aziden zu vermeiden, wurde – ausgehend von Bromiden, Mesylaten oder Tosylaten
– ein Eintopfverfahren entwickelt. Neben den untersuchten Phosphoramidaten
konnten auch N,N-disubstituierte Phosphinamidate durch die Lewis-Säure- oder
Alkylhalogenid-katalysierte Umlagerung in Ausbeuten von 36% bis 83% gewonnen
werden. Wird die Reaktion von Phosphiten und Aziden unter wässrigen
Bedingungen durchgeführt, erfolgt anstelle der Alkylierung des Stickstoffes
die Protonierung zum Phosphoramidat. Erste Versuche zeigten, dass die
Staudinger-Reaktion für die bioorthogonale Umsetzung von Azido-Peptiden
erfolgreich genutzt werden kann und auch unter phys. pH-Wert durchführbar ist.
Basierend auf den anfänglichen Ergebnissen wurde die Staudinger-Reaktion für
die metallfreie, ortsspezifische Funktionalisierung von Peptiden und Proteinen
eingesetzt – beispielsweise zur PEGylierung – und konnte zur chemischen
Phosphorylierung von Proteinen herangezogen werden. Im letzten Teil der Arbeit
wurde die Staudinger Reaktion verwendet, um den einfachen und direkten Zugang
zu Phosphonamidat-haltigen Peptiden zu ermöglichen. Phosphinsäure-Derivate
können durch Silylierung mit Bis(trimethylsilyl) acetamid unter wasser- und
sauerstofffreien Bedingungen in die entsprechenden Phosphonite überführt und
in situ mit den unterschiedlichen arylischen Aziden und Azido-Peptiden
umgesetzt werden. Diese Methode erlaubt darüber hinaus die Durchführung der
Synthese auch an der festen Phase, sodass nach Abspaltung vom Harz die
gewünschten Phosphonamidat-haltigen Peptide mit hoher Reinheit erhalten werden
können. Außerordentlich vorteilhaft ist die entwickelte Synthese zur
Herstellung von Phosphonamidaten mit freier Hydroxylgruppe, die besonders
instabil sind und aufwendige Entschützungs- und Reinigungsmethoden nicht
zulassen. Bei dem Einsatz von alkylischen Aziden kam es zu einer interessanten
Nebenreaktion. Basierend auf umfangreiche Untersuchungen zu der Struktur der
Nebenprodukte, Einfluss der Reaktionsbedingungen und 15N-
Markierungsexperimenten, konnte ein Mechanismus für die Nebenreaktion
vorgeschlagen werden. Erster Schritt ist dabei die Zersetzung des Phosphazids
in Methyl P-Phenylphosphonamidat und eine Diazoverbindung. Letztere kann mit
einem weiteren Äquivalent des Silylphosphonits zu dem dargestellten
Nebenprodukt reagieren
Melitaea phoebe subsp. caucasica Staudinger 1870
No full textM. phoebe caucasica Staudinger, 1870 [TL: “Kindermann ganz ähnliche Stücke im Caucasus fing (?- Helenendorf; Kindermann leg.)”]. The name caucasica was preoccupied by M. didyma caucasica Staudinger, 1861 and the name was replaced first by M. phoebe ottonis Fruhstorfer 1917. A lectotype female and a paralectotype male were designated by Nekrutenko (Hesselbarth et al. 1995: 2: 1028) from the Staudinger collection, housed at Zoologisches Museum der Humboldt Universität, Berlin (figs 5A, B, C & 6A, B, C). Verity subsequently also proposed a replacement name, caucasicola Verity, 1919, this being a synonym of ottonis. Kemal & Koçak (2011: 44) used the name ‘ Melitaea (Cinclidia) (phoebe) sextilis Jachontov, 1909 ’ as a replacement name giving it subspecific(?) status; however, Jachontov (1909: 285) used this name for a variety of second generation M. phoebe and, so far as the authors are aware, no author since has used the name sextilis in favour of ottonis Fruhstorfer, 1917. In fact the M. phoebe species group portrayed by Kemal & Koçak (2011: 44), in their article on eastern Mediterranean butterflies, included M. punica, a species absent from the eastern Mediterranean. This perpetuates confusion, which the first author with others has been trying to resolve. Hesselbarth et al. (1995: 3, Tafel 80/81: figs 30– 33 ♂; Tafel 82/83: figs 1– 4 ♀) placed ottonis as a synonym of M. phoebe. Although the lectotype female does not show all the characters typical of M. phoebe, for instance the underside submarginal black arches do not touch the intervening veins (see Fig. 5B), the paralectotype underside (Fig. 6B) certainly shows all the characters typical of M. phoebe. Recent authors, such Tshikolovets (2011: 497; 2003: plate 24: figs 16 m. and 17 f.), Tshikolovets et al. (2014: 318–319), van Oorschot & Coutsis (2014: 60) and Russell & Tennent (2016: 45, note 22) have all agreed that this is a subspecies of M. phoebe and not M. ornata, with which the present authors concur.Published as part of Russell, Peter J. C., Lukhtanov, Vladimir A. & Tennent, W. John, 2022, Reassessment of the status of some European and Asian Melitaea taxa described as subspecies of Melitaea phoebe ([Denis & Schiffermüller], 1775), with designations of lectotypes where appropriate (Lepidoptera: Nymphalidae), pp. 25-38 in Zootaxa 5141 (1) on page 26, DOI: 10.11646/zootaxa.5141.1.2, http://zenodo.org/record/657762
Note sur Charaxes kheili Staudinger et Charaxes northeotti W. Rothschild, avec les descriptions des femelles [Lep. Nymphalidae]
No full textMinig André, Plantrou Jacques. Note sur Charaxes kheili Staudinger et Charaxes northeotti W. Rothschild, avec les descriptions des femelles [Lep. Nymphalidae]. In: Bulletin de la Société entomologique de France, volume 80 (9-10), Novembre-décembre 1975. pp. 275-285
Epidola stigma STAUDINGER 1859
No full textEpidola stigma STAUDINGER, 1859 N e w t o C r e t e. E x a m i n e d m a t e r i a l. 333, 4 km S. Topolia, 28.vii.-1.viii.2001, leg. Fibiger et al., genitalia slide Hendriksen 3269 (ZMUC).Published as part of Karsholt, Ole & Huemer, Peter, 2017, Review of Gelechiidae (Lepidoptera) from Crete, pp. 159-190 in Linzer biologische Beiträge 49 (1) on page 171, DOI: 10.5281/zenodo.535659
Prof. Th. W. Adorno and the author Hans Erich Nossack.
No full textProf. Th. W. Adorno and the author Hans Erich Nossack at a reception of Insel Verlag, Buchmesse Frankfurt 1966LB
Lepidopteren-Fauna Kleinasien's
No full textvon Dr. O. StaudingerTeil1: 307 Seiten ; Teil 2: 277 Seiten ; Teil 3 (Nachträge): 71 Seiten(Separatdruck aus den "Horae Societatis cutomologicae rossicae". Bd. XIV)Handschriftliches Geschenkexlibris: "Seinem verehrten Freund Professor H. Frey vom Verfasser O. Staudinger" 011253956_0001 Exemplar der ETH-BIBExlibrisstempel: "Entomologische Sammlung der eidgen. techn. Hochschule Zürich" 011145977_0001 Exemplar der ETH-BI
Głęboki wykop obiektowy w Heidelbergu
No full textGłęboka obudowa liniowa Emunds + Staudinger (E + S) stanowi ekonomiczną alternatywę dla tradycyjnych metod szalowania głębokich wykopów. Dobrym tego potwierdzeniem jest realizacja głębokiego wykopu obiektowego w Heidelbergu w południowych Niemczech
Chondrostega hyrcana Staudinger 1871
No full textChondrostega hyrcana Staudinger, 1871 Chondrostega pastrana hyrcana Staudinger, 1871, Cat. Lep. Eur., Ed. 2: 67. TL: Persien. References: Staudinger 1871: 67; Wiltshire 1952: 188. Distribution (Map 3): Turkmenia, southern Tadjikistan. - In Iran: Golestan, Semnan and Khorasan provinces. MAP 3. Chondrostega hyrcana Staudinger, 1871. Bionomics. The species is native to arid biotopes and is univoltine with flight period from mid August to mid October. Females wingless. Caterpillars on various lower plants, observed from Artemisia spp. (Asteraceae), Astragalus spp., Onobrychus spp. (Fabaceae = Leguminosae), Malcolmia turkestanica (Brassicaceae), Carex pachystilis (Carecaceae), Calligonum griseum (Polygonaceae). Eggs hibernate. Material Examined: male, type, Persia (ZMHU); 2 males, Schah-Kuh (ZISP); 1 male, Balla-Ishan, 3.V 1894, Anger leg. (ZISP); 1 male, Kazan-dzhak, 12.V 1894, leg. Anger (ZISP); 3 males, Transcaspia, Gaudan, V- VII, leg. Anger (ZISP). (HMIM): Golestan: Ramian N, Shahpasand, 420 m, 04.VI. 1982, leg. Hashemi; Shah- Kuh-Bala, Elburs Mnts., 2500 m, 21.VII. 1999, leg. Hofamnn A., Meineke J.U. & Mollet B.; Almeh W, Parke-Melli-Golestan, 1650 m, 23–24.VIII. 1983, leg. Borumand & Pazuki. Khorasan: Almeh, Park-e-Melli- Golestan, 1590–1600 m, 01.IX. 1987, leg. Pazuki A.; Shekar-ab, Tandureh, Dareh Gaz, 2100 m, 11.VIII. 1993, leg. Ebrahimi E. & Badii M. Semnan: Kashidar, N Sahahrud, 1250 m, 21.VIII. 1982, leg. Hashemi; Kalpush, Shahrud, 1300 m, 25–26.VIII. 1982, leg. Hashemi; Nardin, NE Shahrud, 1800 m, 23–24.VIII. 1982, leg. Hashemi.Published as part of Zolotuhin, Vadim V. & Zahiri, Reza, 2008, The Lasiocampidae of Iran (Lepidoptera), pp. 1-52 in Zootaxa 1791 on page 6, DOI: 10.5281/zenodo.27431
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