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A convenient route to optically pure α-alkyl-β-(sec-amino)alanines.

Olma A, Lasota A, Kudaj A - Amino Acids (2011)

Bottom Line: The cyclization of N-Boc-α-alkylserines to corresponding β-lactones under Mitsunobu reaction conditions and the ring opening with heterocyclic amines (pyrrolidine, piperidine, morpholine and thiomorpholine) produced N-Boc-α-alkyl-β-(sec-amino)alanines.The removal of the Boc group gives di-hydrochlorides of non-protein amino acids.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924, Lodz, Poland. aleksandra.olma@p.lodz.pl

ABSTRACT
The cyclization of N-Boc-α-alkylserines to corresponding β-lactones under Mitsunobu reaction conditions and the ring opening with heterocyclic amines (pyrrolidine, piperidine, morpholine and thiomorpholine) produced N-Boc-α-alkyl-β-(sec-amino)alanines. The removal of the Boc group gives di-hydrochlorides of non-protein amino acids.

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R = CH3 (a), CH(CH3)3 (b), CH2CH(CH3)2 (c), CH2C6H5 (d)
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Sch1: R = CH3 (a), CH(CH3)3 (b), CH2CH(CH3)2 (c), CH2C6H5 (d)

Mentions: Scheme 1 outlines our method of synthesis of (R)-α-alkyl-β-(sec-amino) alanines. Heterocyclic amines, such as pyrrolidine, piperidine, morpholine and thiomorpholine were used as nitrogen nucleophiles.Scheme 1


A convenient route to optically pure α-alkyl-β-(sec-amino)alanines.

Olma A, Lasota A, Kudaj A - Amino Acids (2011)

R = CH3 (a), CH(CH3)3 (b), CH2CH(CH3)2 (c), CH2C6H5 (d)
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3351611&req=5

Sch1: R = CH3 (a), CH(CH3)3 (b), CH2CH(CH3)2 (c), CH2C6H5 (d)
Mentions: Scheme 1 outlines our method of synthesis of (R)-α-alkyl-β-(sec-amino) alanines. Heterocyclic amines, such as pyrrolidine, piperidine, morpholine and thiomorpholine were used as nitrogen nucleophiles.Scheme 1

Bottom Line: The cyclization of N-Boc-α-alkylserines to corresponding β-lactones under Mitsunobu reaction conditions and the ring opening with heterocyclic amines (pyrrolidine, piperidine, morpholine and thiomorpholine) produced N-Boc-α-alkyl-β-(sec-amino)alanines.The removal of the Boc group gives di-hydrochlorides of non-protein amino acids.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924, Lodz, Poland. aleksandra.olma@p.lodz.pl

ABSTRACT
The cyclization of N-Boc-α-alkylserines to corresponding β-lactones under Mitsunobu reaction conditions and the ring opening with heterocyclic amines (pyrrolidine, piperidine, morpholine and thiomorpholine) produced N-Boc-α-alkyl-β-(sec-amino)alanines. The removal of the Boc group gives di-hydrochlorides of non-protein amino acids.

Show MeSH