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

被引：6
作者：
Olma, A. [1 ]
Lasota, A. [1 ]
Kudaj, A. [1 ]
机构：
[1] Tech Univ Lodz, Inst Organ Chem, PL-90924 Lodz, Poland
来源：
AMINO ACIDS | 2012年 / 42卷 / 06期
关键词：
alpha-Alkyl-beta-(sec-amino)alanines; N-Boc-alpha-alkylserines beta-lactones; alpha; alpha-Disubstituted glycines; Mitsunobu reaction; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC GLYCINE; EFFICIENT SYNTHESIS; BINDING-PROPERTIES; BETA-LACTONES; AMINO-ACIDS; SERINE; ANALOGS; TRANSFORMATION; EQUIVALENTS;
D O I：
10.1007/s00726-011-1055-3
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The cyclization of -Boc-alpha-alkylserines to corresponding beta-lactones under Mitsunobu reaction conditions and the ring opening with heterocyclic amines (pyrrolidine, piperidine, morpholine and thiomorpholine) produced -Boc-alpha-alkyl-beta-(-amino)alanines. The removal of the Boc group gives di-hydrochlorides of non-protein amino acids.
引用
收藏
页码：2525 / 2528
页数：4
相关论文
共 33 条
[1]   ON THE MECHANISM OF THE "TRIPHENYLPHOSPHINE-AZODICARBOXYLATE (MITSUNOBU REACTION) ESTERIFICATION [J].
ADAM, W ;
NARITA, N ;
NISHIZAWA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1843-1845
[2]   CONFORMATIONAL STUDIES ON ALAMETHICIN [J].
BURGESS, AW ;
LEACH, SJ .
BIOPOLYMERS, 1973, 12 (12) :2691-2712
[3]   Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids [J].
Cativiela, Carlos ;
Diaz-de-Villegas, Maria D. .
TETRAHEDRON-ASYMMETRY, 2007, 18 (05) :569-623
[4]   TOTAL SYNTHESIS OF (-)-TANTAZOLE-B [J].
FUKUYAMA, T ;
XU, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8449-8450
[5]   Asymmetric synthesis of quaternary α-amino acid derivatives and their fluorinated analogues [J].
Fustero, Santos ;
Sanchez-Rosello, Maria ;
Baez, Claribel ;
del Pozo, Carlos ;
Garcia Ruano, Jose L. ;
Aleman, Jose ;
Marzo, Leyre ;
Parra, Alejandro .
AMINO ACIDS, 2011, 41 (03) :559-573
[6]   ENZYMATIC-SYNTHESIS OF NONPROTEIN BETA-SUBSTITUTED ALANINES AND SOME HIGHER HOMOLOGS IN PLANTS [J].
IKEGAMI, F ;
MURAKOSHI, I .
PHYTOCHEMISTRY, 1994, 35 (05) :1089-1104
[7]   Role of the countercation in diastereoselective alkylations of pyramidalized bicyclic serine enolates.: An easy approach to α-benzylserine [J].
Jimenez-Oses, Gonzalo ;
Aydillo, Carlos ;
Busto, Jesus H. ;
Zurbano, Maria M. ;
Peregrina, Jesus M. ;
Avenoza, Alberto .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5399-5402
[8]  
KAMINSKI ZJ, 1973, SYNTHESIS-STUTTGART, P792
[9]   A convenient transformation of α-alkylserines into α-halogenomethyl-α-alkylglycines [J].
Kudaj, Adam ;
Olma, Aleksandra .
TETRAHEDRON LETTERS, 2008, 49 (45) :6445-6447
[10]   An efficient synthesis of optically pure α-alkyl-β-azido- and α-alkyl-β-aminoalanines via ring opening of 3-amino-3-alkyl-2-oxetanones [J].
Kudaj, Adam ;
Olma, Aleksandra .
TETRAHEDRON LETTERS, 2007, 48 (38) :6794-6797
1234