Boc-protected Amino Acids Research Articles

Simple, High-Yield Synthesis of Polyhedral Carborane Amino Acids

Boron neutron capture therapy (BNCT) is a form of binary cancer therapy that offers the potential of delivering spatially selective, high linear energy transfer radiation to the target cells while sparing surrounding normal tissue. We have demonstarted a versatile, general method for the conversion of o- ,m-, and p-carborane to their corresponding Boc-protected amino acids. Heterobifunctional polyhedral carboranes are exceedingly rare in the literature, and the amino acids prepared by this general method may prove to be valuable synthons for use in the synthesis of tumor-seeking compounds for BNCT or PDT. Morever, these conformationally constrained amino acids should be particularly interesting for use in peptide synthesis. The dihedral angle between the carbon atoms of these polyhedra increases in the order 60{degree} (ortho), 110{degree} (meta), and 180{degree} (para), allowing the peptide chemist to select a desired conformation. 11 refs.

A convenient synthesis of chiral peptide nucleic acid (PNA) monomers

Chiral peptide nucleic acid monomers containing amino acid side chains can be easily prepared from the BOC-protected amino acids.

Zinc mediated addition of active halides to a glycine cation equivalent: Synthesis of N-Boc-L-propargylglycine

The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with α-chymotrypsin affords N-Boc-L-propargylglycine in 99% e.e..

Intramolecular alkylation of carboxylic acids: application to the synthesis of boc-protected cyclic amino acids

A new synthesis of Boc-protected cyclic amino acids is described as an application of an unreported method of lithium diisopropylamide-induced cyclisation of ω-chloro carboxylic acids containing a protected amine functionin the chain.

Continuous flow solid (gel) phase peptide synthesis using unsupported ultra-high load polymers.

A simple, manually operated, continuous flow apparatus is described for solid (gel) phase peptide synthesis. The approach uses an unsupported phenolic bead form core network at an initial matrix loading of 5 mmol g-1, the theoretical maximum. The synthesis is performed in a flow reactor under low pressure conditions. "Layered displacement" of reagent solutions and washing solvents is an essential feature that has been developed to facilitate efficient peptide synthesis. The usefulness of the present system in conjunction with N alpha Boc protected amino acids is illustrated by the syntheses of [Leu5]-enkephalin and dermorphin. The potential for scale up synthesis has also been investigated.

Lipidic peptides. IV. Penicillin and cephalosporin amide conjugates with lipidic amino acids and their oligomers

A series lipidic amide conjugates ( 2b, c, 3b, c, 4b-d, 5b and c) of β-lactam antibiotics were synthesised using mixed anhydride methods to couple the Boc-protected lipidic amino acids ( 1a and b) and oligomer ( 1c) to a variety of penicillins and cephalosporins. Conjugates ( 2b, c, 3b, 4b-d and 5b) showed weak to moderate activity in vitro and were only weakly active in vivo against the non-β-lactamase producing stain S. aureus 663E.

A facile synthesis of statine and analogs by reduction of .beta.-keto esters derived from Boc-protected amino acids. HPLC analyses of their enantiomeric purity

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA facile synthesis of statine and analogs by reduction of .beta.-keto esters derived from Boc-protected amino acids. HPLC analyses of their enantiomeric purityJuergen Maibaum and Daniel H. RichCite this: J. Org. Chem. 1988, 53, 4, 869–873Publication Date (Print):February 1, 1988Publication History Published online1 May 2002Published inissue 1 February 1988https://doi.org/10.1021/jo00239a035RIGHTS & PERMISSIONSArticle Views814Altmetric-Citations64LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (670 KB) Get e-Alerts Get e-Alerts