An SN2 deprotection of synthetic peptides with a low concentration of hydrofluoric acid in dimethyl sulfide: evidence and application in peptide synthesis

No abstract is available for this paper.

• Publication year

  1983

• Venue

  Journal of the American Chemical Society

• Publication date

  1983-10-01

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1021/JA00359A014
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• No references are available for this paper.

• Surface-engineered antibacterial and anti-calculus coatings on polyester via chitosan–amino acid grafting and silver–ion coordination

  2026cites this paper
• Linker-Free Synthesis of Antimicrobial Peptides Using a Novel Cleavage Reagent: Characterisation of the Molecular and Ionic Composition by nanoESI-HR MS

  2023cites this paper
• Lewis Acid Probe for Basicity of Sulfide Electrolytes Investigated by 11B Solid-State NMR

  2023cites this paper
• Identification of B Cell and T Cell Epitopes Using Synthetic Peptide Combinatorial Libraries

  2022cites this paper
• Production of high-complexity frameshift neoantigen peptide microarrays

  2020cites this paper
• A novel platform for peptide-mediated affinity capture and LC-MS/MS identification of host receptors involved in Plasmodium invasion.

  2020cites this paper
• p‐Methoxyphenol: A potent and effective scavenger for solid‐phase peptide synthesis

  2020influential citation
• Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations.

  2019cites this paper
• Dynamic Assembly of a Trithioorthoformate-Capped Cage and Its Endohedral Inclusion of a Methine Group.

  2019cites this paper
• The renascence of continuous-flow peptide synthesis - an abridged account of solid and solution-based approaches.

  2018cites this paper
• An efficient reduction of N-substituted carbonylimidazolides into formamides by NaBH4

  2017cites this paper
• Discovery of Mixed Pharmacology Melanocortin-3 Agonists and Melanocortin-4 Receptor Tetrapeptide Antagonist Compounds (TACOs) Based on the Sequence Ac-Xaa1-Arg-(pI)DPhe-Xaa4-NH2.

  2017cites this paper
• Fmoc-Amox, A Suitable Reagent for the Introduction of Fmoc

  2017cites this paper
• Bioinspired Design and Oriented Synthesis of Immunogenic Site-Specifically Penicilloylated Peptides.

  2016cites this paper
• Differences in the Abilities to Mechanically Eliminate Activation Energies for Unimolecular and Bimolecular Reactions

  2016cites this paper
• Methods, setup and safe handling for anhydrous hydrogen fluoride cleavage in Boc solid-phase peptide synthesis

  2015cites this paper
• Fibrillar gels via the self-assembly of poly(L-glutamate)-based statistical copolymers

  2015cites this paper
• Peptide Oxidation/Reduction Side Reactions

  2015cites this paper
• Protein Ligation and Total Synthesis II

  2015cites this paper
• Chemical synthesis of a polypeptide backbone derived from the primary sequence of the cancer protein NY‐ESO‐1 enabled by kinetically controlled ligation and pseudoprolines

  2015cites this paper
• Solid phase protein chemical synthesis.

  2015cites this paper
• Discovery of a Potent and Selective α3β4 Nicotinic Acetylcholine Receptor Antagonist from an α-Conotoxin Synthetic Combinatorial Library

  2014cites this paper
• Identification of Tetrapeptides from a Mixture Based Positional Scanning Library That Can Restore nM Full Agonist Function of the L106P, I69T, I102S, A219V, C271Y, and C271R Human Melanocortin-4 Polymorphic Receptors (hMC4Rs)

  2014cites this paper
• Sodium Borohydride Reduction of Carbamoyl Azide Function: A Synthesis of N‐Protected N′‐Formyl‐gem‐diaminoalkyl Derivatives

  2013cites this paper
• Discovery of novel antinociceptive α-conotoxin analogues from the direct in vivo screening of a synthetic mixture-based combinatorial library.

  2013cites this paper
• Oxidative folding and preparation of α‐conotoxins for use in high‐throughput structure–activity relationship studies

  2013cites this paper
• Efficient access to highly pure β-amyloid peptide by optimized solid-phase synthesis

  2012cites this paper
• Peptide based modulators of prostate specific kallikrein-related peptidases 2 and 3

  2012cites this paper
• Tandem thiol switch synthesis of peptide thioesters via N-S acyl shift on thiazolidine.

  2011cites this paper
• Acid-catalyzed tandem thiol switch for preparing peptide thioesters from mercaptoethyl esters.

  2011cites this paper
• Linkers for Solid‐Phase Peptide Synthesis

  2011cites this paper
• Peptides derived from Mycobacterium tuberculosis Rv2301 protein are involved in invasion to human epithelial cells and macrophages

  2011cites this paper
• Solid Phase and Combinatorial Chemistry in the Heterocyclic Field

  2011cites this paper
• Potential-dependent membrane permeabilization and mitochondrial aggregation caused by anticancer polyarginine-KLA peptides.

  2010cites this paper
• Controlled in situ preparation of A beta(1-42) oligomers from the isopeptide "iso-A beta(1-42)", physicochemical and biological characterization.

  2010cites this paper
• 1H-NMR conformational study of a synthetic peptide derived from the consensus sequence of annexins.

  2009cites this paper
• Chemical synthesis of five tubulin antigenic sequences. Production and characterization of their corresponding anti-tubulin monospecific antibodies.

  2009cites this paper
• Comparison of 55% TFA/CH2Cl2 and 100% TFA for Boc group removal during solid-phase peptide synthesis.

  2009cites this paper
• Structure activity of C-terminal modified analogs of Ac-CCK-7.

  2009cites this paper
• Synthesis of biologically active porcine secretin and [ITyr10] porcine secretin.

  2009cites this paper
• Solid phase synthesis of peptides containing the non-hydrolysable analog of (O)phosphotyrosine, p(CH2PO3H2)Phe : application to the synthesis of 344-357 sequences of the β2 adrenergic receptor

  2009cites this paper
• Unprotected peptides as building blocks for branched peptides and peptide dendrimers.

  2009cites this paper
• Chemical synthesis of a neurotoxic polypeptide from the sea anemone Stichodactyla helianthus.

  2009cites this paper
• Structure-activity studies of vasoactive intestinal peptide (VIP): cyclic disulfide analogs.

  2009cites this paper
• Solid-phase peptide synthesis: a silver anniversary report.

  2009cites this paper
• Mild, orthogonal solid-phase peptide synthesis: use of N alpha-dithiasuccinoyl (Dts) amino acids and N-(iso-propyldithio)carbonylproline, together with p-alkoxybenzyl ester anchoring linkages.

  2009cites this paper
• Solid phase synthesis of a fully active analogue of cholecystokinin using the acid-stable Boc-Phe (p-CH2) SO3H as a substitute for Boc-Tyr(SO3H) in CCK8.

  2009cites this paper
• Cleavage of a model peptide at its glycine residue by alkaline mercuric oxycyanide.

  2009cites this paper
• Deprotection of N(in)-formyl group on tryptophan by application of new reagent, 1,2-dimethylethylendiamine in aqueous solution.

  2009cites this paper
• Solid phase synthesis of gastrin I. Comparison of methods utilizing strong acid for deprotection and cleavage.

  2009cites this paper
• A synthetic protein corresponding to the entire vpr gene product from the human immunodeficiency virus HIV-1 is recognized by antibodies from HIV-infected patients.

  2009cites this paper
• Potentiation of glucose-induced insulin release in islets by desHis1[Glu9]glucagon amide.

  2009cites this paper
• Some problems in direct Edman degradation of peptidyl-resins

  2009cites this paper
• Synthetic linear and cyclic glucagon antagonists.

  2009cites this paper
• Two-step hard acid deprotection/cleavage procedure for solid phase peptide synthesis.

  2009cites this paper
• Solid phase synthesis of bioadhesive analogue peptides with trifluoromethanesulfonic acid cleavage from PAM resin

  2009cites this paper
• Reactions of C‐terminal ω‐amino acid residues in liquid hydrogen fluoride

  2009cites this paper
• A novel strategy for the synthesis of the cysteine-rich protective antigen of the malaria merozoite surface protein (MSP-1). Knowledge-based strategy for disulfide formation.

  2009cites this paper
• An improved solid-phase synthesis of a difficult-sequence peptide using hexafluoro-2-propanol.

  2009cites this paper
• Use of the Npys thiol protection in solid phase peptide synthesis. Application to direct peptide-protein conjugation through cysteine residues.

  2009cites this paper
• D-enantiomers of 15-residue cecropin A-melittin hybrids.

  2009cites this paper
• Synthesis and biological evaluation of mouse growth hormone-releasing factor.

  2009cites this paper
• Efficient approach to synthesis of two-chain asymmetric cysteine analogs of receptor-binding region of transforming growth factor-alpha.

  2009cites this paper
• Solid phase synthesis and biological activity of mast cell degranulating (MCD) peptide: a component of bee venom

  2009cites this paper
• Structure-function analysis of a series of glucagon-like peptide-1 analogs.

  2009cites this paper
• Solid‐phase synthesis of bombesin by continuous flow procedure using Fmoc‐amino acids*

  2009cites this paper
• Ethylcarbamoyl protection for cysteine in the preparation of peptide-conjugate immunogens.

  2009cites this paper
• Mapping the receptor-recognition site of human transforming growth factor-alpha.

  2009cites this paper
• Chemical synthesis of insulin-like growth factor II.

  2009cites this paper
• Solid-phase synthesis, metal binding and folding properties of caulimovirus-related 'zinc finger'.

  2009cites this paper
• Synthesis of biologically active analogs of the dodecapeptide a-factor mating pheromone of Saccharomyces cerevisiae.

  2009cites this paper
• Potential-dependent permeabilization of plasma membrane by the peptide BTM-P1 derived from the Cry11Bb1 protoxin.

  2009cites this paper
• Deprotection of the indole (N(ind))-formyl (For) group on tryptophan employing a new reagent, N,N'-dimethylethylendiamine (DMEDA) in an aqueous solution.

  2009cites this paper
• A novel antifungal peptide designed from the primary structure of a natural antimicrobial peptide purified from Argopecten purpuratus hemocytes.

  2009cites this paper
• Synthesis and antibacterial action of cecropin and proline-arginine-rich peptides from pig intestine.

  2009cites this paper
• Synthesis and assay of tyrosinated analogs of a crustacean pigment‐dispersing neuropeptide hormone

  2009cites this paper
• Synthesis of a new carrier for immunization: polytuftsin. Two examples of its use with peptides selected in the hepatitis B surface antigen.

  2009cites this paper
• Design, synthesis and antibacterial activity of cecropin-like model peptides.

  2009cites this paper
• Chemical synthesis and characterization of peptides and oligomeric proteins designed to form transmembrane ion channels.

  2009cites this paper
• Synthesis and properties of cholecystokinin-releasing peptide (monitor peptide), a 61-residue trypsin inhibitor.

  2009cites this paper
• Structure activity studies of tryptophan30 modified analogs of Ac-CCK-7.

  2009cites this paper
• Side reactions in solid-phase peptide synthesis and their applications.

  2009cites this paper
• Improved approach for anchoring N alpha-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis.

  2009cites this paper
• Synthesis and biological evaluation of pNPY fragments.

  2009cites this paper
• Solid phase synthesis of thymosin β9

  2009cites this paper
• Solid-phase synthesis of a nonadecapeptide coded for by the v-myb oncogene.

  2009cites this paper
• Chemical synthesis and characterization of the epidermal growth factor-like module of human complement protease C1r.

  2009cites this paper
• Solution structure of the toxic octapeptide, lophyrotomin.

  2009cites this paper
• Synthesis and immunological characterization of a 134-mer synthetic peptide corresponding to the N-terminal half of the HIV-1 nucleoprotein, p24.

  2009cites this paper
• Evaluation of laminin peptide fragments labeled with indium-111 for the potential imaging of malignant tumors.

  2009cites this paper
• Cleavage and deprotection of peptides on MBHA-resin with hydrogen bromide.

  2009cites this paper
• Novel version of Multiple Antigenic Peptide allowing incorporation on a cysteine functionalized lysine tree.

  2009cites this paper
• Synthesis and study of normal, enantio, retro, and retroenantio isomers of cecropin A-melittin hybrids, their end group effects and selective enzyme inactivation.

  2009cites this paper
• Synthesis of biologically active transforming growth factor alpha.

  2009cites this paper
• Synthesis and hormonal activity of [Tyr22] glucagon and [desHis1, Tyr22] glucagon.

  2009cites this paper
• Antibacterial peptides designed as analogs or hybrids of cecropins and melittin.

  2009cites this paper
• Synthesis and conformational studies of peptides encompassing the carboxy-terminal helix of thermolysin.

  2009cites this paper
• Solid-phase synthesis of the native sequence of horse heart cytochrome c-(66-104)-nonatriacontapeptide and of a C-terminal carboxyamide analog selectively modified at Met-80.

  2009cites this paper
• Allyl-based groups for side-chain protection of amino-acids.

  2009cites this paper
• Improved deprotection of cysteine‐containing peptides in HF

  2009cites this paper