Diverse organo-peptide macrocycles via a fast and catalyst-free oxime/intein-mediated dual ligation.

نویسندگان

  • Maragani Satyanarayana
  • Francesca Vitali
  • John R Frost
  • Rudi Fasan
چکیده

Macrocyclic Organo-Peptide Hybrids (MOrPHs) can be prepared from genetically encoded polypeptides via a chemoselective and catalyst-free reaction between a trifunctional oxyamino/amino-thiol synthetic precursor and an intein-fusion protein incorporating a bioorthogonal keto group.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Macrocyclization of organo-peptide hybrids through a dual bio-orthogonal ligation: insights from structure-reactivity studies.

Macrocycles constitute an attractive structural class of molecules for targeting biomolecular interfaces with high affinity and specificity. Here, we report systematic studies aimed at exploring the scope and mechanism of a novel chemo-biosynthetic strategy for generating macrocyclic organo-peptide hybrids (MOrPHs) through a dual oxime-/intein-mediated ligation reaction between a recombinant pr...

متن کامل

Rsc_cc_c1cc13533c 1..3

Macrocyclic peptides and peptide-based structures have attracted significant interest as a source of chemical probes and therapeutic agents. While peptides and peptidomimetics in rigidified configurations can be prepared synthetically, genetic encoding offers the advantage to couple the creation of vast chemical libraries (10–10) with ultrahigh-throughput screeningmethods. Notable approaches in...

متن کامل

Synthesis of bicyclic organo-peptide hybrids via oxime/intein-mediated macrocyclization followed by disulfide bond formation.

A new strategy is described to generate bicyclic peptides that incorporate non-peptidic backbone elements starting from recombinant polypeptide precursors. These compounds are produced via a one-pot, two-step sequence, in which peptide macrocyclization by means of a bifunctional oxyamine/1,3-amino-thiol synthetic precursor is followed by intramolecular disulfide formation between the synthetic ...

متن کامل

Ribosomal Synthesis of Macrocyclic Peptides in Vitro and in Vivo Mediated by Genetically Encoded Aminothiol Unnatural Amino Acids.

A versatile method for orchestrating the formation of side chain-to-tail cyclic peptides from ribosomally derived polypeptide precursors is reported. Upon ribosomal incorporation into intein-containing precursor proteins, designer unnatural amino acids bearing side chain 1,3- or 1,2-aminothiol functionalities are able to promote the cyclization of a downstream target peptide sequence via a C-te...

متن کامل

Preparation of Reactive and Thermal Stable Hyperbranched Graft Copolymers/ Clay Nanocomposite via ‘Living’ Free Radical Polymerization

Exfoliated poly (Chloromethyl styrene-co-styrene)-g-polyacrylonitryle/organo- modified montmorillonite [P(CMSt-co-St)-g-PAN/O-MMT] nanocomposite was synthesized through solution intercalation method by using atom transfer and nitroxide mediated radical polymerization. At first, poly (chloromethyl styrene-costyrene) copolymer was synthesized by nitroxide - mediated “living” free radical polyme...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 48 10  شماره 

صفحات  -

تاریخ انتشار 2012