Convenient solid-phase synthesis of oligopeptides using pentacoordinated phosphoranes with amino acid residue as building blocks

Hepatoprotective Principles and Other Chemical Constituents from the Mycelium of Phellinus linteus

“…In addition to phellinulins A–N ( 1 – 14 ), nineteen known compounds, including phellilins A–C ( 15 – 17 ) [ 29 ], γ-ionylideneacetic acid ( 18 ) [ 28 ], ergosta-(7,9(11),22t)-trien-3β-ol [ 30 ], (−)-cinnamolide [ 31 ], ergosterol peroxide [ 32 ], 6β-hydroxycinnamolide [ 33 ], cinnamolide-3β-ol [ 34 ], 5-hydroxy-4-phenyl-5 H -furan-2-one [ 35 ], p -hydroxybenzaldehyde [ 36 ], lumichrome [ 37 ], phenylalanine-leucine [ 38 ], phenylalanine-isoleucine [ 39 ], phenylalanine [ 40 ], proline-valine [ 41 ], phenylalanine-proline [ 42 ], proline-leucine [ 43 ] and phenylalanine-alalinine [ 44 ] were also identified by comparison of their physical and spectroscopic data with those reported.…”

Chiral Hypervalent, Pentacoordinated Phosphoranes

“…The process was repeated to give oligopeptides. The final oligopeptide was liberated from the resin by treatment with TFA [124] (Scheme 69). …”

“…The process was repeated to give oligopeptides. The final oligopeptide was liberated from the resin by treatment with TFA [124] (Scheme 69). O-Trimethylsilyl derivatives of spirophosphoranes 177 containing an amino acid residue were formed by the cyclisation of the corresponding cyclic amides 176 [123] (Scheme 68).…”

Peptide‐Chain Elongation Using Unprotected Amino Acids in a Micro‐Flow Reactor

“…The amidation proceeds smoothly because D is soluble against an organic solvent andt he trimethylsilyl (TMS) groups can be removedd uring the aqueous work-up process to afford C.P remodification, however,r equires as toichiometric amount of an expensive silylating agent. [13] Premodifications of unprotected amino acids B to cyclic compounds E using silyl, [14] boron, [15] phosphorous, [16] or phosgene equivalentr eagents [17] or hexafluoroacetone [18] as shown in Scheme 1(III) were also reported. The subsequent aqueous work-upp rocess affords peptides with af ree N-terminus.…”