Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

Wünsch M, Schröder DC, Fröhr T, Teichmann L, Hedwig S, Janson N, Belu C, Simon J, Heidemeyer S, Holtkamp P, Rudlof J, et al. (2017)
Beilstein Journal of Organic Chemistry 13: 2428-2441.

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Abstract / Bemerkung
The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at C-alpha, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 N-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral N-sulfinylimines, which were reacted with (trimethylsilyl) ethynyllithium to afford diastereomerically pure N-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the Ca of amino acids. Whereas propargylamines with (cyclo) alkyl substituents can be prepared in a direct manner, residues with polar functional groups require suitable protective groups. The presence of particular functional groups in the side chain in some cases leads to remarkable side reactions of the alkyne moiety. Thus, electron-withdrawing substituents in the C-alpha-position facilitate a base induced rearrangement to alpha, beta-unsaturated imines, while azide-substituted propargylamines form triazoles under surprisingly mild conditions. A panel of propargylamines bearing fluoro or chloro substituents, polar functional groups, or basic and acidic functional groups is accessible for the use as precursors of peptidomimetics.
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Beilstein Journal of Organic Chemistry
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13
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2428-2441
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Wünsch M, Schröder DC, Fröhr T, et al. Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics. Beilstein Journal of Organic Chemistry. 2017;13:2428-2441.
Wünsch, M., Schröder, D. C., Fröhr, T., Teichmann, L., Hedwig, S., Janson, N., Belu, C., et al. (2017). Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics. Beilstein Journal of Organic Chemistry, 13, 2428-2441. doi:10.3762/bjoc.13.240
Wünsch, M., Schröder, D. C., Fröhr, T., Teichmann, L., Hedwig, S., Janson, N., Belu, C., Simon, J., Heidemeyer, S., Holtkamp, P., et al. (2017). Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics. Beilstein Journal of Organic Chemistry 13, 2428-2441.
Wünsch, M., et al., 2017. Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics. Beilstein Journal of Organic Chemistry, 13, p 2428-2441.
M. Wünsch, et al., “Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics”, Beilstein Journal of Organic Chemistry, vol. 13, 2017, pp. 2428-2441.
Wünsch, M., Schröder, D.C., Fröhr, T., Teichmann, L., Hedwig, S., Janson, N., Belu, C., Simon, J., Heidemeyer, S., Holtkamp, P., Rudlof, J., Klemme, L., Hinzmann, A., Neumann, B., Stammler, H.-G., Sewald, N.: Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics. Beilstein Journal of Organic Chemistry. 13, 2428-2441 (2017).
Wünsch, Matthias, Schröder, David C., Fröhr, Tanja, Teichmann, Lisa, Hedwig, Sebastian, Janson, Nils, Belu, Clara, Simon, Jasmin, Heidemeyer, Shari, Holtkamp, Philipp, Rudlof, Jens, Klemme, Lennard, Hinzmann, Alessa, Neumann, Beate, Stammler, Hans-Georg, and Sewald, Norbert. “Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics”. Beilstein Journal of Organic Chemistry 13 (2017): 2428-2441.

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1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics.
Kracker O, Góra J, Krzciuk-Gula J, Marion A, Neumann B, Stammler HG, Nieß A, Antes I, Latajka R, Sewald N., Chemistry 24(4), 2018
PMID: 29160605
Structure-Activity Relationship of Propargylamine-Based HDAC Inhibitors.
Wünsch M, Senger J, Schultheisz P, Schwarzbich S, Schmidtkunz K, Michalek C, Klaß M, Goskowitz S, Borchert P, Praetorius L, Sippl W, Jung M, Sewald N., ChemMedChem 12(24), 2017
PMID: 29120081

108 References

Daten bereitgestellt von Europe PubMed Central.

A nonpeptidic cathepsin S activity-based probe for noninvasive optical imaging of tumor-associated macrophages.
Verdoes M, Edgington LE, Scheeren FA, Leyva M, Blum G, Weiskopf K, Bachmann MH, Ellman JA, Bogyo M., Chem. Biol. 19(5), 2012
PMID: 22633413
Identification of selective, nonpeptidic nitrile inhibitors of cathepsin s using the substrate activity screening method.
Patterson AW, Wood WJ, Hornsby M, Lesley S, Spraggon G, Ellman JA., J. Med. Chem. 49(21), 2006
PMID: 17034136
Substrate activity screening: a fragment-based method for the rapid identification of nonpeptidic protease inhibitors.
Wood WJ, Patterson AW, Tsuruoka H, Jain RK, Ellman JA., J. Am. Chem. Soc. 127(44), 2005
PMID: 16262416
Characterization and optimization of selective, nonpeptidic inhibitors of cathepsin S with an unprecedented binding mode.
Inagaki H, Tsuruoka H, Hornsby M, Lesley SA, Spraggon G, Ellman JA., J. Med. Chem. 50(11), 2007
PMID: 17469812
Exploration of cathepsin S inhibitors characterized by a triazole P1-P2 amide replacement.
Moss N, Xiong Z, Burke M, Cogan D, Gao DA, Haverty K, Heim-Riether A, Hickey ER, Nagaraja R, Netherton M, O'Shea K, Ramsden P, Schwartz R, Shih DT, Ward Y, Young E, Zhang Q., Bioorg. Med. Chem. Lett. 22(23), 2012
PMID: 23084902
Asymmetric synthesis of amines using tert-butanesulfinamide.
Xu HC, Chowdhury S, Ellman JA., Nat Protoc 8(11), 2013
PMID: 24157547
Identification of a new class of nonpeptidic inhibitors of cruzain.
Brak K, Doyle PS, McKerrow JH, Ellman JA., J. Am. Chem. Soc. 130(20), 2008
PMID: 18435536
Nonpeptidic tetrafluorophenoxymethyl ketone cruzain inhibitors as promising new leads for Chagas disease chemotherapy.
Brak K, Kerr ID, Barrett KT, Fuchi N, Debnath M, Ang K, Engel JC, McKerrow JH, Doyle PS, Brinen LS, Ellman JA., J. Med. Chem. 53(4), 2010
PMID: 20088534
Identification and evaluation of small molecule pan-caspase inhibitors in Huntington's disease models.
Leyva MJ, Degiacomo F, Kaltenbach LS, Holcomb J, Zhang N, Gafni J, Park H, Lo DC, Salvesen GS, Ellerby LM, Ellman JA., Chem. Biol. 17(11), 2010
PMID: 21095569
Functional studies of Plasmodium falciparum dipeptidyl aminopeptidase I using small molecule inhibitors and active site probes.
Deu E, Leyva MJ, Albrow VE, Rice MJ, Ellman JA, Bogyo M., Chem. Biol. 17(8), 2010
PMID: 20797610
Highly Stereoselective Synthesis of Terminal Chloro-Substituted Propargylamines and Further Functionalization.
Jordan S, Starks SA, Whatley MF, Turlington M., Org. Lett. 17(19), 2015
PMID: 26368832
Rhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions.
Lee SI, Park SY, Park JH, Jung IG, Choi SY, Chung YK, Lee BY., J. Org. Chem. 71(1), 2006
PMID: 16388622

Wünsch M, Senger J, Schultheisz P, Schwarzbich S, Michalek C, Klaß M, Goskowitz S, Borchert P, Jung M, Sewald N., 0
"Clicktophycin-52": a bioactive cryptophycin-52 triazole analogue.
Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N., Org. Lett. 12(5), 2010
PMID: 20131817

Johansson J, Hermansson E, Nordén B, Kann N, Beke-Somfai T., 2014

Kracker O, Góra J, Krzciuk-Gula J, Marion A, Neumann B, Stammler H-G, Nieß A, Antes I, Latajka R, Sewald N., 0
Universal peptidomimetics.
Ko E, Liu J, Perez LM, Lu G, Schaefer A, Burgess K., J. Am. Chem. Soc. 133(3), 2010
PMID: 21182254

Temperini A, Capperucci A, Degl’Innocenti A, Terlizzi R, Tiecco M., 2010

Weix D, Ellman J., 2005

Aggarwal V, Barbero N, McGarrigle E, Mickle G, Navas R, Suárez J, Unthank M, Yar M., 2009
N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines.
Ellman JA, Owens TD, Tang TP., Acc. Chem. Res. 35(11), 2002
PMID: 12437323
Thermal rearrangement of tert-butylsulfinamide.
Arava VR, Gorentla L, Dubey PK., Beilstein J Org Chem 7(), 2011
PMID: 21286388

Huang Z, Zhang M, Wang Y, Qin Y., 2005

Higashibayashi S, Tohmiya H, Mori T, Hashimoto K, Nakata M., 2004

Liu G, Cogan D, Owens T, Tang T, Ellman J., 1999
Microwave-assisted solvent-free synthesis of enantiomerically pure N-(tert-butylsulfinyl)imines.
Collados JF, Toledano E, Guijarro D, Yus M., J. Org. Chem. 77(13), 2012
PMID: 22694241

Liu G, Cogan D, Ellman J., 1997
Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals.
Foti MC, Johnson ER, Vinqvist MR, Wright JS, Barclay LR, Ingold KU., J. Org. Chem. 67(15), 2002
PMID: 12126405
The total synthesis of tubulysin D.
Peltier HM, McMahon JP, Patterson AW, Ellman JA., J. Am. Chem. Soc. 128(50), 2006
PMID: 17165738
Design, synthesis, and biological properties of highly potent tubulysin D analogues.
Patterson AW, Peltier HM, Sasse F, Ellman JA., Chemistry 13(34), 2007
PMID: 17828721
Expedient synthesis of N-methyl tubulysin analogues with high cytotoxicity.
Patterson AW, Peltier HM, Ellman JA., J. Org. Chem. 73(12), 2008
PMID: 18479168

González-Gómez J, Foubelo F, Yus M., 2009
Synthesis and applications of tert-butanesulfinamide.
Robak MT, Herbage MA, Ellman JA., Chem. Rev. 110(6), 2010
PMID: 20420386

Chuang C, Gallucci J, Hart D., 1988
Chemoselective Alkylations with N- and C-Metalated Nitriles.
Yang X, Nath D, Fleming FF., Org. Lett. 17(19), 2015
PMID: 26390098

Mancuso A, Huang S-L, Swern D., 1978

Cogan D, Liu G, Ellman J., 1999

Guijarro D, Pablo Ó, Yus M., 2009
Diastereoselective alkynylation of N-p-tolylsulfinylimines with aluminum acetylides.
Turcaud S, Berhal F, Royer J., J. Org. Chem. 72(21), 2007
PMID: 17880139

Carreira E, Du J., 1995

Nishikawa T, Ino A, Isobe M., 1994

Levin V, Dilman A, Belyakov P, Struchkova M, Tartakovsky V., 2008
Solid-phase synthesis and chemical space analysis of a 190-membered alkaloid/terpenoid-like library.
Moura-Letts G, Diblasi CM, Bauer RA, Tan DS., Proc. Natl. Acad. Sci. U.S.A. 108(17), 2011
PMID: 21451137

Ding C-H, Chen D-D, Luo Z-B, Dai L-X, Hou X-L., 2006

Alzeer J, Vasella A., 1995

Ernst A, Gobbi L, Vasella A., 1996
Site-specific chemical protein conjugation using genetically encoded aldehyde tags.
Rabuka D, Rush JS, deHart GW, Wu P, Bertozzi CR., Nat Protoc 7(6), 2012
PMID: 22576105

Brewer G, Johnson M., 1953
Phenylalanine and Phenylglycine Analogues as Arginine Mimetics in Dengue Protease Inhibitors.
Weigel LF, Nitsche C, Graf D, Bartenschlager R, Klein CD., J. Med. Chem. 58(19), 2015
PMID: 26367391
Identification and role of ionizing functional groups at the active center of Rhodotorula gracilis D-amino acid oxidase.
Pollegioni L, Harris CM, Molla G, Pilone MS, Ghisla S., FEBS Lett. 507(3), 2001
PMID: 11696364
Selectivity of commonly used pharmacological inhibitors for cystathionine β synthase (CBS) and cystathionine γ lyase (CSE).
Asimakopoulou A, Panopoulos P, Chasapis CT, Coletta C, Zhou Z, Cirino G, Giannis A, Szabo C, Spyroulias GA, Papapetropoulos A., Br. J. Pharmacol. 169(4), 2013
PMID: 23488457
Predicting the activity of antimicrobial peptides with amino acid topological information.
Shu M, Yu R, Zhang Y, Wang J, Yang L, Wang L, Lin Z., Med Chem 9(1), 2013
PMID: 22741801
The role of fluorine in medicinal chemistry.
Shah P, Westwell AD., J Enzyme Inhib Med Chem 22(5), 2007
PMID: 18035820
Applications of Fluorine in Medicinal Chemistry.
Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA., J. Med. Chem. 58(21), 2015
PMID: 26200936
New antivirals and antiviral resistance.
Prober CG., Adv. Exp. Med. Biol. 549(), 2004
PMID: 15250510
On the molecular mechanism of the antiviral activity of trifluorothymidine.
Heidelberger C., Ann. N. Y. Acad. Sci. 255(), 1975
PMID: 171993
Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors.
Corbett JW, Ko SS, Rodgers JD, Gearhart LA, Magnus NA, Bacheler LT, Diamond S, Jeffrey S, Klabe RM, Cordova BC, Garber S, Logue K, Trainor GL, Anderson PS, Erickson-Viitanen SK., J. Med. Chem. 43(10), 2000
PMID: 10821714
Efavirenz: a decade of clinical experience in the treatment of HIV.
Maggiolo F., J. Antimicrob. Chemother. 64(5), 2009
PMID: 19767318
Are all antidepressants really the same? The case of fluoxetine: a systematic review.
Cipriani A, Barbui C, Brambilla P, Furukawa TA, Hotopf M, Geddes JR., J Clin Psychiatry 67(6), 2006
PMID: 16848644
Role of fluoxetine in anorexia nervosa.
Kim SS., Ann Pharmacother 37(6), 2003
PMID: 12773080
A general and regioselective synthesis of 5-trifluoromethyl-pyrazoles.
Foster RS, Jakobi H, Harrity JP., Org. Lett. 14(18), 2012
PMID: 22934538
Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1.
Corbett JW, Ko SS, Rodgers JD, Jeffrey S, Bacheler LT, Klabe RM, Diamond S, Lai CM, Rabel SR, Saye JA, Adams SP, Trainor GL, Anderson PS, Erickson-Viitanen SK., Antimicrob. Agents Chemother. 43(12), 1999
PMID: 10582878

Magnus N, Confalone P, Storace L., 2000

Corbett J., 2002
An efficient chiral moderator prepared from inexpensive (+)-3-carene: synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963.
Kauffman GS, Harris GD, Dorow RL, Stone BR, Parsons RL Jr, Pesti JA, Magnus NA, Fortunak JM, Confalone PN, Nugent WA., Org. Lett. 2(20), 2000
PMID: 11009360

Magueur G, Crousse B, Bonnet-Delpon D., 2005

Magueur G, Crousse B, Bonnet-Delpon D., 2008
The chemistry of trifluoromethyl imines and related acetals derived from fluoral.
Begue JP, Bonnet-Delpon D, Crousse B, Legros J., Chem Soc Rev 34(7), 2005
PMID: 15965538

Bravo P, Crucianelli M, Vergani B, Zanda M., 1998

Asensio A, Bravo P, Crucianelli M, Farina A, Fustero S, Soler J, Meille S, Panzeri W, Viani F, Volonterio A., 2001

Crucianelli M, De F, Lazzaro F, Malpezzi L, Volonterio A, Zanda M., 2004

Lazzaro F, Crucianelli M, De F, Frigerio M, Malpezzi L, Volonterio A, Zanda M., 2004

Greier G., 1983

Xiao H, Huang Y, Qing F-L., 2010

Kuduk S, Di C, Pitzenberger S, Tsou N., 2006

Vartanyan S, Badanyan S., 1967
Rapid assembly and in situ screening of bidentate inhibitors of protein tyrosine phosphatases.
Srinivasan R, Uttamchandani M, Yao SQ., Org. Lett. 8(4), 2006
PMID: 16468749
Mechanism-based tumor-targeting drug delivery system. Validation of efficient vitamin receptor-mediated endocytosis and drug release.
Chen S, Zhao X, Chen J, Chen J, Kuznetsova L, Wong SS, Ojima I., Bioconjug. Chem. 21(5), 2010
PMID: 20429547

Corrie J, Hlubucek J, Lowe G., 1977

Koreeda M, Yang W., 1994
α-Acetylenic Derivatives of Amines
AUTHOR UNKNOWN, 1979
α-Acetylenic Derivatives of α-Amino Acids
AUTHOR UNKNOWN, 1980
Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3 + 2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions.
Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E, Vaccaro L., J. Org. Chem. 70(16), 2005
PMID: 16050724

Huisgen R., 1963

Panday N, Meyyappan M, Vasella A., 2000

Panday N, Vasella A., 2000

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