Synthesis of protected norcysteines for SPPS compatible with Fmoc strategy
نویسندگان
چکیده
منابع مشابه
Synthesis of Fmoc-protected trans-4-methylproline.
Fmoc-protected trans-4-methylproline was synthesized starting from D-serine. The chiral scaffold of serine in the form of olefinated Garner's aldehyde 3 was used to control the diastereoselective formation of the new stereocenter on the hydrogenation of allylic alcohol 4. The diastereoselectivity (syn/anti ratio) of the process was 86:14, attained with Raney nickel. Hydrogen migration seems not...
متن کاملEfficient synthesis of Fmoc-protected phosphinic pseudodipeptides: Building blocks for the synthesis of matrix metalloproteinase inhibitors.
A convenient route for the synthesis of Fmoc-protected phosphinic dipeptide building blocks is described. The protected amino acid isosteres benzyloxycarbonyl aminomethyl phosphinic acid (glycine surrogate), benzyl α-isopropyl acrylate (valine surrogate), and benzyl α-isobutyl acrylate (leucine surrogate) were synthesized starting from commercially available materials. Reaction of either the va...
متن کاملScalable synthesis of Fmoc-protected GalNAc-threonine amino acid and T(N) antigen via nickel catalysis.
The highly α-selective and scalable synthesis of the Fmoc-protected GalNAc-threonine amino acid and TN antigen in gram scale (0.5-1 g) is described. The challenging 1,2-cis-2-amino glycosidic bond is addressed through a coupling of threonine residues with C(2)-N-ortho-(trifluoromethyl)benzylidenamino trihaloacetimidate donors mediated by Ni(4-F-PhCN)4(OTf)2. The desired 1,2-cis-2-amino glycosid...
متن کاملSynthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine.
A Boc-protecting group strategy for Fmoc-based PNA (peptide nucleic acid) oligomerization has been developed for thymine, 2,6-diaminopurine (DAP) and 2-aminopurine (2AP). The monomers may be used interchangeably with standard Fmoc PNA monomers. The DAP monomer was incorporated into a PNA and was found to selectively bind to T (ΔT(m)≥ +6 °C) in a complementary DNA strand. The 2AP monomer showed ...
متن کاملConvenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
The peptide nucleic acid backbone Fmoc-AEG-OBn has been synthesized via a scalable and cost-effective route. Ethylenediamine is mono-Boc protected, then alkylated with benzyl bromoacetate. The Boc group is removed and replaced with an Fmoc group. The synthesis was performed starting with 50 g of Boc anhydride to give 31 g of product in 32% overall yield. The Fmoc-protected PNA backbone is a key...
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ژورنال
عنوان ژورنال: Tetrahedron Letters
سال: 2007
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2007.05.082