Publications

Review the scientific articles where the Bachem team has contributed to peptide research and peptide synthesis.

Bachem – Insights into Innovative and Sustainable Peptide Chemistry and Technology by the Leading Independent Manufacturer of TIDES
Sandip Jadhav, Wolfgang Seufert, Carolin Lechner, Ralph Schönleber
CHIMIA, 75, 476-479 (2021)

Harnessing polarity and viscosity to identify green binary solvent mixtures as viable alternatives to DMF in solid-phase peptide synthesis
Vincent Martin,  Sandip Jadhav,  Peter H. G. Egelund, Raphael Liffert, Henrik Johansson Castro, Tobias Krüger, Kim F. Haselmann, Sebastian Thordal Le Quement, Fernando Albericio, Frank Dettner, Carolin Lechner,  Ralph Schönleber  and  Daniel Sejer Pedersen
Green Chem., Advance Article (2021)

Replacing DMF in solid-phase peptide synthesis: varying the composition of green binary solvent mixtures as a tool to mitigate common side-reactions
Sandip Jadhav, Vincent Martin, Peter H. G. Egelund, Henrik Johansson Castro, Tobias Krüger, Franziska Richner, Sebastian Thordal Le Quement, Fernando Albericio, Frank Dettner, Carolin Lechner, Ralph Schönleber and  Daniel Sejer Pedersen
Green Chem., Advance Article (2021)

Traceless parallel peptide purification by a first-in-class reductively cleavable linker system featuring a safety-release
Robert Zitterbart, Nadja Berger, Oliver Reimann, Gavin T. Noble, Stephan Lüdtke, Dominik Sarma, Oliver Seitz
Chem. Sci., 12, 2389-2396 (2021)

Sequence sensitivity and pH dependence of maleimide conjugated N‐terminal cysteine peptides to thiazine rearrangement
Isaiah N. Gober, Alexander J. Riemen, Matteo Villain
J. Pept. Sci., e3323 (2021)

The aspartimide problem persists: Fluorenylmethyloxycarbonyl-solid-phase peptide synthesis (Fmoc-SPPS) chain termination due to formation of N-terminal piperazine-2,5-diones.
D.Samson, D.Rentsch, M.Minuth, T.Meier and G.Loidl
J. Pept. Sci. 25, e3193 (2019)

Substitution determination of Fmoc-substituted resins at different wavelengths
S.Eissler, M.Kley, D.Bächle, G.Loidl, T.Meier, and D.Samson
J. Pept. Sci., 23, 757-762 (2017)

Scope and limitations of Fmoc chemistry SPPS-based approaches to the total synthesis of insulin Lispro via ester insulin
B.Dhayalan, K.Mandal, N.Rege, M.A.Weiss, S.H.Eitel, T.Meier, R.O.Schoenleber, and S.B.Kent
Chem. Eur. J.23(7),1709-1716 (2017)

Chemical glycosylation of peptides
Ch.McGee and J.Thundimadathil
Pharma Horizon 1(2) (2017)

Review: Glucagon-like peptide 1 (GLP-1) in the treatment of diabetes / GLP-1 agonist peptides against type 2 diabetes are promising targets for patients with poor Hb1Ac control
A.Gangakhedkar and J.Thundimadathil
Genetic Engineering & Biotechnology News35(13) (2015)

Bachem – Insights into peptide chemistry achievements by the world’s leading independent manufacturer of peptides
M.Mergler, G.Loidl, M.Diekmann, and F.Dick
Chimia67, 874-880 (2013)

Quantitative assessment of preloaded 4-alkoxybenzyl alcohol resins for solid-phase peptide syntheses by 1D and 2D HR-MAS NMR
D.Rentsch, C.Stahelin, M.Obkircher, R.Hany, M.Simeunovic, D.Samson, G.Loidl, and F.Dick
ACS Comb. Sci. 14, 613-620 (2012)

Analogs of the sea anemone potassium channel blocker ShK for the treatment of autoimmune diseases
C.Beeton, M.W.Pennington and R.S.Norton
Inflamm. Allergy Drug Targets 10, 313-321 (2011)

Efficient stereocontrolled synthesis of (S)-Fmoc-β-nitroalanine via oxidation of oxime
S.S.Chauhan and H.J.Wilk
Tetrahedron Lett. 51, 3340-3343 (2010)

Recent developments to encourage the synthesis of complex peptides
T.Vorherr
PharmaChem 9 (3/4), 19-23 (2010)

Critical parameters for solid-phase manufacturing of therapeutic peptides
T.Vorherr
Chim. Oggi 28, 22-25 (2010)

Potassium channel modulation by a toxin domain in matrix metalloprotease 23
S.Rangaraju, K.K.Khoo, Z.-P.Feng, G.Crossley, D.Nugent, I.Khaytin, V.Chi, C.Pham, P.Calabresi, M.W.Pennington, R.S.Norton and K.G.Chandy
J. Biol. Chem. 285, 9124-9136 (2010)

Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary
S.Chauhan
Tetrahedron Lett. 50, 6913-6915 (2009)

Engineering a stable and selective peptide blocker of the Kv1.3 channel in T lymphocytes
M.W.Pennington, C.Beeton, C.A.Galea, B.J.Smith, V.Chi, K.P.Monaghan, A.Garcia, S.Rangaraju, A.Giuffrida, D.Plank, G.Crossley, D.Nugent, I.Khaytin, Y.LeFievre, I.Peshenko, C.Dixon, S.Chauhan, A.Orzel, T.Inoue, X.Hu, R.V.Moore, R.S.Norton and K.G.Chandy
Mol. Pharmacol. 75, 762–773 (2009)

Peptides as drugs – Molecular evolvement in recent years
T.Vorherr
PharmaChem 7 (9), 13-16 (2008)

Novel polymyxin derivatives carrying only three positive charges are effective antibacterial agents
M.Vaara, J.Fox, G.Loidl, O.Siikanen, J.Apajalahti, F.Hansen, N.Frimodt-Møller, J.Nagai, M.Takano and T.Vaara Antimicrob. Agents Chemother. 52, 3229-3236 (2008)

Imaging of effector memory T cells during a delayed-type hypersensitivity reaction and suppression by Kv1.3 channel block
M.P.Matheu, C.Beeton, A.Garcia, V.Chi, S.Rangaraju, O.Safrina, K.Monaghan, M.I.Uemura, D.Li, S.Pal, L.M.de la Maza, E.Monuki, A.Flügel, M.W.Pennington, I.Parker, K.G.Chandy and M.D.Cahalan
Immunity 29, 1-13 (2008)

Formation of Fmoc-β-alanine during Fmoc-protections with Fmoc-OSu
M.Obkircher, C.Stähelin and F.Dick
J. Pept. Sci. 14, 763-766 (2008)

The D-diastereomer of ShK toxin selectively blocks voltage-gated K+ channels and inhibits T lymphocyte proliferation
C.Beeton, B.J.Smith, J.K.Sabo, G.Crossley, D.Nugent, I.Khaytin, V.Chi, K.G.Chandy, M.W.Pennington and R.S.Norton
J. Biol. Chem. 283, 988-997 (2008)

Targeting effector memory T-cells with Kv1.3 blockers
H.Wulff and M.Pennington
Curr. Opin. Drug Discov. Devel. 10, 438-445 (2007)

Targeted tyrosine iodination in a multi-tyrosine vasopressin analog
J.A.Durr, M.Blankenship, S.S.Chauhan and M.W.Pennington
J. Pept. Sci. 13, 756-761 (2007)

Characterization of the functional properties of the voltage-gated potassium channel Kv1.3 in human CD4+ T lymphocytes
L.Hu, M.Pennington, Q.Jiang, K.A.Whartenby and P.A.Calabresi
J. Immunol. 179, 4563-4570 (2007)

Purification of sparingly soluble peptides by temporary solubilization
F.Dick, M.Mergler, G.Loidl, R.Schönleber and T.Vorherr
Proceedings of the 29th European Peptide Symposium, Gdansk (2006). Kenes International, Switzerland (2007)

Efficient synthesis of protected L-phosphonophenylalanine (Ppa) derivatives suitable for solid phase peptide synthesis
S.Chauhan, A.Varshney, B.Verma and M.W.Pennington
Tetrahedron Lett.. 48, 4051-4054 (2007)

Purification: The bottleneck in peptide production
T.Vorherr
Spec. Chem. 27, 40-42 (2007)

Approaches for the purification of sparingly soluble peptides
T.Vorherr
Chim. Oggi 25, 22-24 (2007)

Kv1.3 channels are a therapeutic target for T cell-mediated autoimmune diseases
C.Beeton, H.Wulff, N.E.Standifer, P.Azam, K.M.Mullen, M.W.Pennington, A.Kolski-Andreaco, E.Wei, A.Grino, D.R.Counts, P.H.Wang, C.J.LeeHealey, B.S.Andrews, A.Sankaranarayanan, D.Homerick, W.W.Roeck, J.Tehranzadeh, K.L.Stanhope, P.Zimin, P.J.Havel, S.Griffey, H.-G.Knaus, G.T.Nepom, G.A.Gutman, P.A.Calabresi and K.G.Chandy
Proc. Natl. Acad. Sci. USA 103, 17414–17419 (2006)

Potassium channels Kv1.3 and Kv1.5 are expressed on blood-derived dendritic cells in the central nervous system
K.M.Mullen, M.Rozycka, H.Rus, L.Hu, C.Cudrici, E.Zafranskaia, M.W.Pennington, D.C.Johns, S.I.V.Judge and P.A.Calabresi
Ann. Neurol. 60, 118–127 (2006)

Peptides: Impact of new technologies on chemical production
T.Vorherr
PharmaChem 5 (7/8), 14-17 (2006)

Peptide thioester preparation based on an N-S acyl shift reaction mediated by a thiol ligation auxiliary
T.Kawakami, M.Sumida, K.Nakamura, T.Vorherr and S.Aimoto
Tetrahedron Lett. 46, 8805-8807 (2005)

The aspartimide problem in Fmoc-based SPPS. Part III
M.Mergler and F.Dick
J. Pept. Sci.11, 650-657 (2005)

Bachem, a Swiss speciality cGMP-manufacturer: History and future prospects
T.Vorherr, F.Dick and B.Sax
Chimia 59, 25-27 (2005)

A short practical synthesis of 2′-deoxymugineic acid
S.Singh, G.Crossley, S.Ghosal, Y.Lefievre and M.Pennington
Tetrahedron Lett. 46, 1419-1421 (2005)

Targeting effector memory T cells with a selective peptide inhibitor of Kv1.3 channels for therapy of autoimmune diseases
C.Beeton, M.W.Pennington, H.Wulff, S.Singh, D.Nugent, G.Crossley, I.Khaytin, P.A.Calabresi, C.Chen, G.A.Gutman and K.G.Chandy
Mol. Pharmacol. 67, 1369-1981 (2005)

Bass hepcidin synthesis, solution structure, antimicrobial activities and synergism, and in vivo hepatic response to bacterial infections
X.Lauth, J.J.Babon, J.A.Stannard, S.Singh, V.Nizet, J.M.Carlberg, V.E.Ostland, M.W.Pennington, R.S.Norton and M.E.Westerman
J. Biol. Chem. 280, 9272-9282 (2005)

Potassium channel blockade by the sea anemone toxin ShK for the treatment of multiple sclerosis and other autoimmune diseases
R.S.Norton, M.W.Pennington and H.Wulff
Curr. Med. Chem. 11, 3141-3152 (2004)

Asymmetric synthesis of (R)- and (S)-a-methylcysteine
S.Singh
Recent Res. Devel. Organic Chem. 8, 323-339 (2004)

K+ Channel expression during B cell differentiation: Implications for immunomodulation and autoimmunity
H.Wulff, H.G.Knaus, M.Pennington and K.G.Chandy
J. Immunol. 173, 776-786 (2004)

Efficient asymmetric synthesis of (S)- and (R)-N-Fmoc-S-Trityl-a-methylcysteine using camphorsultam as a chiral auxiliary
S.Singh, S.J.Rao and M.W.Pennington
J. Org. Chem. 69, 4551-4554 (2004)

K+ channels as targets for specific immunomodulation
K.G.Chandy, H.Wulff, C.Beeton, M.Pennington, G.A.Gutman and M.D.Cahalan
Trends Pharmacol. Sci. 25, 280-289 (2004)

Rational design and synthesis of selective BACE-1 inhibitors
S.F.Brady, S.Singh, M.C.Crouthamel, M.K.Holloway, C.A.Coburn, V.M.Garsky, M.Bogusky, M.W.Pennington, J.P.Vacca, D.Hazuda and M.T.Lai
Bioorg. Med. Chem. Lett. 14, 601-604 (2004)

A very bright future for cGMP-manufacturing of peptides
T.Vorherr
Chim. Oggi 21, 14-15 (2003)

The aspartimide problem in Fmoc-based SPPS. Part II
M.Mergler, F.Dick, B.Sax, C.Stähelin and T.Vorherr
J. Pept. Sci. 9, 518-526 (2003)

The caspase-like sites of proteasomes: substrate specificity, new inhibitors and substrates, and allosteric interactions with the trypsin-like sites
A.F.Kisselev, M.Garcia-Calvo, H.S.Overkleeft, E.Peterson, M.W.Pennington, H.L.Ploegh, N.A.Thornberry and A.L.Goldberg
J. Biol. Chem. 278, 35869-35877 (2003)

The voltage-gated Kv1.3 K+ channel in effector memory T cells as new target for MS
H.Wulff, P.A.Calabresi, R.Allie, S.Yun, M.Pennington, C.Beeton and K.G.Chandy
J. Clin. Invest. 111, 1703-1713 (2003)

An efficient asymmetric synthesis of Fmoc-L-cyclopentylglycine via diastereoselective alkylation of glycine enolate equivalent
S.Singh and M.Pennington
Tetrahedron Lett. 44, 2683-2685 (2003)

The aspartimide problem in Fmoc-based SPPS. Part I
M.Mergler, F.Dick, B.Sax, P.Weiler and T.Vorherr
J. Pept. Sci. 9, 36-46 (2003)

A novel fluorescent toxin to detect and investigate Kv1.3 channel upregulation in chronically activated T lymphocytes
M.D.Lanigan, H.Wulff, S.Singh, S.Botsko, G.Crossley, G.A.Gutman, M.D.Cahalan, M.Pennington and K.G.Chandy
J. Biol. Chem. 278, 9928-9937 (2003)

Addition of o-aminobenzoic acid during Fmoc solid phase synthesis of a fluorogenic substrate containing 3-nitrotyrosine
S.Singh, I.Khaytin, S.Botsko, G.Crossley, D.K.Plank, Y.Lefievre, F.Giuffrida and M.W.Pennington
Lett. Pept. Sci. 9, 221-225 (2002)

Mutating a critical lysine in ShK toxin alters its binding configuration in the pore-vestibule region of the voltage-gated potassium channel, Kv1.3
M.D.Lanigan, K.Kalman, Y.Lefievre, M.W.Pennington, K.G.Chandy and R. S.Norton
Biochemistry 41, 11963-11971 (2002)

Synthesis and application of an auxiliary group for chemical ligation at the X-Gly site
J.Vizzavona, F.Dick and T.Vorherr
Bioorg. Med. Chem. Lett. 12, 1963-1965 (2002)

Selective blockade of T lymphocyte K channels ameliorates experimental autoimmune encephalomyelitis, a model for multiple sclerosis
C.Beeton, H.Wulff, J.Barbaria, O.Clot-Faybesse, M. Pennington, D.Bernard, M. D.Cahalan, K.G.Chandy and E.Béraud
Proc. Natl. Acad. Sci. USA 98, 13942-13947 (2001)

Designed peptide analogues of the potassium channel blocker ShK toxin
M.D.Lanigan, M.W.Pennington, Y.Lefievre, H.Rauer and R.S.Norton
Biochemistry 40, 15528-15537 (2001)

Synthesis and application of Fmoc-His(3-Bum)-OH
M.Mergler, F.Dick, B.Sax, J.Schwindling and T.Vorherr
J. Pept. Sci. 7, 502-510 (2001)

Potassium channels in T lymphocytes: toxins to therapeutic immunosuppressants
K.G.Chandy, M.Cahalan, M.Pennington, R.S.Norton, H.Wulff and G.A.Gutman
Toxicon 39, 1269-1276 (2001)

A helical capping motif in ShK toxin and its role in helix stabilization
M.D.Lanigan, J.E.Tudor, M.W.Pennington and R.S.Norton
Biopolymers 58, 422-436 (2001)

Protected peptide p-nitroanilides by solid-phase synthesis
M.Mergler, F.Dick, J.Gosteli and R.Nyfeler.
Lett. Pept. Sci. 7, 1-7 (2000)

Synthesis and evaluation of enantiomeric purity of protected alpha-amino and peptide aldehydes
Th.Mindt, U.Michel and F.Dick
Helv. Chim. Acta 82, 1960-1968 (1999)

The role of disulfide bonds in the structure and potassium channel blocking activity of ShK toxin
M.W.Pennington, M.Lanagin, K.Kalman, V.M.Mahnir, H.Rauer, C.T.McVaugh, D.Behm, D.Donaldson, K.G.Chandy, W.R.Kem and R.S.Norton
Biochemistry 38, 14549-14558 (1999)

Structural conservation of the pores of calcium-activated and voltage-gated potassium channels determined by a sea anemone toxin
H.Rauer, M.W.Pennington, M.Cahalan and K.G.Chandy
J. Biol. Chem. 274, 21885-21892 (1999)

Sea anemone toxins as templates for the design of immunosuppressant drugs
W.R.Kem, M.W.Pennington and R.S.Norton
Perspect. Drug Discov. Design. 15/16, 111-129 (1999)

SASRINTM. A review of its manifold applications including many useful procedures
M.Mergler
Brochure published by BACHEM (1st ed. 1995, 2nd revised and enlarged ed. 1999)

Polymeric diphenyldiazomethane. A useful resin for SPPS and solid-phase organic chemistry
M.Mergler and R.Nyfeler
Proceedings of the 5th Int. Symp. Innovation and Perspectives in SPPS, London (1997).
Mayflower Scientific Ltd., Birmingham (1999)

SASRINTM Resin, a versatile tool in peptide synthesis and solid phase organic chemistry
M.Mergler, J.Gosteli, P.Grogg, R.Nyfeler and R.Tanner.
Chimia 53, 29-34 (1999)

Solid phase synthesis of fully protected peptide alcohols
M.Mergler, F.Dick, J.Gosteli and R.Nyfeler.
Tetrahedron Lett. 40, 4663-4664 (1999)

Auto-inactivation by cleavage whitin the dimer interface of Kaposi’s sarcoma-associated herpesvirus protease
T.R.Pray, A.M.Nomura, M.W.Pennington and C.S.Craik.
J. Mol. Biol. 289, (2), 197-203 (1999)

Racemization upon activation and coupling to a fluorophore containing building block
p.254 in: Peptides 1998, Proceedings of the 25th European Peptide Symposium,
F.Dick, E.Kulow, R.Nyfeler, B.Rohwedder and T.Vorherr.
August 30 – September 4, 1998, Budapest, Hungary, edited by S. Bajusz and F. Hudecz (1999)