Asymmetric Synthesis of L-[3-C-13] Tryptophan

被引：5

作者：

Takatori, Kazuhiko ^{[1
]}

Lee, Myonghui ^{[1
]}

Kajiwara, Masahiro ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Dept Med Chem, 2-522-1 Noshio, Kiyose, Tokyo 2048588, Japan

来源：

CURRENT RADIOPHARMACEUTICALS | 2008年 / 1卷 / 02期

关键词：

L-[3-C-13] tryptophan; labeled amino acid; chiral glycine equivalent; oxazinone;

D O I：

10.2174/1874471010801020122

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

Synthesis of L-[3-C-13] tryptophan (2) from N,N-dimethyl[C-13] formamide (4) and Dellaria's oxazinone 1 as a chiral glycine equivalent was achieved. Vilsmeier reaction of indole (5) and N,N-dimethyl[C-13] formamide (4) afforded a good yield of indole-3-[C-13] carbaldehyde (3), which was converted to the bromide 8. Diastereoselective alkylation of the enolate of 1 with the bromide 8 proceeded with high diastereoselectivity to give 9. Ethanolysis, hydrogenolysis and hydrolysis of 9 gave L-[3-C-13] tryptophan (2).

引用

页码：122 / 124

页数：3

共 50 条

[1] An asymmetric synthesis of L-[3-13C]alanine
Takatori, K
Toyama, S
Narumi, S
Fujii, S
Kajiwara, M
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2004, 47 (01): : 91 - 94
[2] An asymmetric synthesis of L-[3-13C]phenylalanine and L-[3-13C]tyrosine from [13C]carbon monoxide
Takatori, K
Nishihara, M
Nishiyama, Y
Kajiwara, M
[J]. TETRAHEDRON, 1998, 54 (52) : 15861 - 15869
[3] STEREOSELECTIVE SYNTHESIS OF STABLE ISOTOPE-LABELED L-ALPHA-AMINO ACIDS - CHEMOMICROBIOLOGICAL SYNTHESIS OF L-[BETA-C-13]-TRYPTOPHAN, L-[2'-C-13]-TRYPTOPHAN, AND L-[1'-N-15]TRYPTOPHAN
UNKEFER, CJ
LODWIG, SN
SILKS, LA
HANNERS, JL
EHLER, DS
GIBSON, R
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1991, 29 (11): : 1247 - 1256
[4] MICROBIAL SYNTHESIS OF L-[N-15]LEUCINE L-[N-15]ISOLEUCINE, AND L-[3-C-13]- AND L-[3'-C-13]ISOLEUCINES STUDIED BY NUCLEAR MAGNETIC-RESONANCE AND GAS-CHROMATOGRAPHY MASS-SPECTROMETRY
KAHANA, ZE
GOPHER, A
DORSMAN, M
LAPIDOT, A
[J]. ANALYTICAL BIOCHEMISTRY, 1988, 174 (02) : 374 - 380
[5] SYNTHESIS OF [2-C-13] QUINOLINE AND [3-C-13] QUINOLINE
BALDWIN, MA
LANGLEY, GJ
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1985, 22 (12): : 1233 - 1238
[6] CARBON-CARBON COUPLING IN [3-C-13(1)]-LABELED TRYPTOPHAN
LONDON, RE
[J]. ORGANIC MAGNETIC RESONANCE, 1981, 17 (02): : 134 - 137
[7] Asymmetric synthesis of L-[4-13C]glutamic acid and glutamine
Takatori, Kazuhiko
Sakamoto, Takuya
Kajiwara, Masahiro
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2006, 49 (05): : 445 - 453
[8] SOLID-PHASE SYNTHESIS OF A TETRAPEPTIDE LABELED WITH C-13 - PREPARATION OF L-[U-C-13]LYSYL-L-[1-C-13]ARGINYL-L-[3-C-13]ASPARTYL-L-[1-C-13]SERINE
HUMBERT, T
MARSURA, A
CUONG, LD
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1992, 31 (03): : 183 - 198
[9] Production of L-[3-C-13] serine from [C-13] formaldehyde and glycine using an enzyme system combined with tetrahydrofolate regeneration
Maeda, H
Takata, K
Toyoda, A
Niitsu, T
Iwakura, M
Shibata, K
[J]. JOURNAL OF FERMENTATION AND BIOENGINEERING, 1997, 83 (01): : 113 - 115
[10] SYNTHESIS OF C-13-LABELLED MEDROXYPROGESTERONE ACETATE WITH 3-C-13 ISOTOPES
RAO, PN
DAMODARAN, KM
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1982, 19 (03): : 415 - 424

← 1 2 3 4 5 →