Synthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs)

Fehrentz, Jean‐Alain; Pothion, Catherine; Califano, Jean-Christophe; Loffet, A.; Martinez, Jean

doi:10.1016/0040-4039(94)88419-6

Cited by 41 publications

(19 citation statements)

References 8 publications

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“…UNCAs can be reduced at room temperature in a few minutes by sodium borohydride in dimethylethylene glycol in the presence of water to produce N-protected fi-amino alcohols 55 (Fehrentz et al, 1994a) in almost quantitative yields. When bulky hydrides were used at lower temperatures, they led to N-protected a-amino aldehydes 56 (Fehrentz et al, 1994b):…”

Section: Synthesis Of Amino Arid Derivatives From N-protected Carboxymentioning

confidence: 99%

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

et al. 1999

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Some of the chemistry of amino acids going on in our laboratory (Laboratoire des Amino acides Peptides et Protéines) is described as well as some mass spectrometry methodology for their characterization particularly on solid supports. Several aspects are presented including: (i) the stereoselective synthesis of natural and unnatural amino acids using 2-hydroxypinan-3-one as chiral auxiliary; (ii) the stereoselective synthesis of natural and unnatural amino acids by deracemization of alpha-amino acids via their ketene derivatives; (iii) the synthesis of alpha-aryl-alpha-amino acids via reaction of organometallics with a glycine cation; (iv) the diastereoselective synthesis of glycosyl-alpha-amino acids; (v) the synthesis of beta-amino acids using alpha-aminopyrrolidinopiperazinediones as chiral templates; (vi) the reactivity of urethane-N-protected N-carboxyanhydrides. To characterize natural and non natural amino acids through their immonium ions by mass spectrometry, some methodology is also described.

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Section: Synthesis Of Amino Arid Derivatives From N-protected Carboxymentioning

confidence: 99%

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

et al. 1999

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“…Carboxy groups have been activated for reduction as active esters [32,33], acid fluorides [34], N-carboxy anhydrides [35] and mixed anhydrides using isobutyl chloroformate [24,36]. The latter has proven to be the best procedure with respect to handling, costs and yields.…”

Section: Preparation Of Fmoc-β-amino Alcohols From Fmoc-α-amino Acidsmentioning

confidence: 99%

Progress in the preparation of peptide aldehydes via polymer supported IBX oxidation and scavenging by threonyl resin

et al. 2005

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Peptide aldehydes are of interest due to their inhibitory properties toward numerous classes of proteolytic enzymes such as caspases or the proteasome. A novel access to peptide aldehydes is described using a combination of solid phase peptide synthesis with polymer-assisted solution phase synthesis based on the oxidation of peptide alcohols with a mild and selective polymer-bound IBX derivative. The oxidation is followed by selective purification via scavenging the peptide aldehyde in a capture-release procedure using threonine attached to an aminomethyl resin. Peptide aldehydes are obtained in excellent purity and satisfying yield. The optical integrity of the C-terminal residue is conserved in a high degree. The procedures are compatible with the use of common side-chain protecting groups. The potential for using the method in parallel approaches is very advantageous. A small collection of new and known peptide aldehydes has been tested for inhibitory activity against caspases 1 and 3.

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“…These intermediates were obtained by reacting ethynylmagnesium bromide with freshly prepared amino aide- hydes 1, either from amino acids [12] or N-carboxy anhydrides [13]. The reaction afforded alcohols 2 with a syn/anti ratio of 6/4 when a solution of ethynylmagnesium bromide was added to compounds 1.…”

Section: R-amino O~-hydroxy Acid Synthesismentioning

confidence: 99%

A convenient method for the synthesis of norstatine derivatives from N-Fmoc or N-Boc amino acids

Kourtal

Pâris

1996

Lett Pept Sci

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Synthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs)

Cited by 41 publications

References 8 publications

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

Progress in the preparation of peptide aldehydes via polymer supported IBX oxidation and scavenging by threonyl resin

A convenient method for the synthesis of norstatine derivatives from N-Fmoc or N-Boc amino acids

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