SYNTHESIS OF DEUTERIUM-LABELED (11S,12R)[H-2(14)]-PALMITIC ACIDS AND (11R,12S)-[H-2(14)]-PALMITIC ACIDS - A FACILE ROUTE TO HIGHLY LABELED FATTY-ACIDS

被引：10

作者：

FROSSL, C ^{[1
]}

BOLAND, W ^{[1
]}

机构：

[1] UNIV KARLSRUHE,INST ORGAN CHEM,RICHARD WILLSTATTER ALLEE 2,D-76131 KARLSRUHE 1,GERMANY

来源：

TETRAHEDRON | 1993年 / 49卷 / 30期

关键词：

D O I：

10.1016/S0040-4020(01)81830-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral, highly deuterated palmitic acids are synthesised from 2,2'-bithienyl in three steps by two alkylations and reductive desulfurisation for the introduction of twelve deuterium atoms. The chiral building blocks are obtained from a,beta-unsaturated acids by enantiospecific reduction with broken cells of the microorganism Clostridium tyrobutyricum.

引用

页码：6613 / 6618

页数：6

共 35 条

[1] SYNTHESIS OF PEPTIDO LEUKOTRIENES LABELED WITH C-14, H-2 OR H-3 - [CYSTEINYL-CO-14], [11,12,14,15-H-2] OR [11,12,14,15-H-3]
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[2] CHIRAL [H-2]-LABELED METHYLENE GROUPS IN TRIENOIC FATTY AND DIENOIC FATTY-ACIDS - A FACILE APPROACH VIA ASYMMETRIC EPOXIDATION OF [H-2]ALLYL ALCOHOLS
NEUMANN, C
BOLAND, W
HELVETICA CHIMICA ACTA, 1990, 73 (03) : 754 - 761
[3] Synthesis of a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains:: (2S,3R,11S,12R,2′"R,5′"Z,11′"S,12′"R)-plakoside A and its (2S,3R,11R,12S,2′"R,5′"Z,11′"R,12′"S) isomer
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Mori, K
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (20) : 3797 - 3809
[4] SYNTHESIS OF [2S-2-H-2]-LABELED AND [2R-2-H-2]-LABELED HEXADECANOIC ACIDS
TULLOCH, AP
CHEMISTRY AND PHYSICS OF LIPIDS, 1982, 30 (04) : 325 - 335
[5] AN EFFICIENT PROCEDURE FOR THE SYNTHESIS AND ISOLATION OF (+)-(2R,3R,11R,12R)-TETRAPHENYL-18-CROWN-6 AND (-)-(2S,3S,11S,12S)-TETRAPHENYL-18-CROWN-6
CROSBY, J
FAKLEY, ME
GEMMELL, C
MARTIN, K
QUICK, A
SLAWIN, AMZ
SHAHRIARIZAVAREH, H
STODDART, JF
WILLIAMS, DJ
TETRAHEDRON LETTERS, 1989, 30 (29) : 3849 - 3852
[6] SYNTHESIS OF FATTY-ACIDS SPECIFICALLY LABELED WITH C-11 IN VARIOUS POSITIONS, INCLUDING H-2 SUBSTITUTION, FOR IN-VIVO STUDIES OF MYOCARDIUM USING PET
KIHLBERG, T
VALIND, S
LANGSTROM, B
NUCLEAR MEDICINE AND BIOLOGY, 1994, 21 (08): : 1053 - 1065
[7] SYNTHESIS OF LEUKOTRIENES LABELED WITH DEUTERIUM - [11,12,14,15-2H4]-LTA4 [11,12,14,15-2H4]-LTC4, [11,12,14,15-2H4]-LTD4 AND [11,12,14,15-2H4]-LTE4
LELLOUCHE, JP
AUBERT, F
NOEL, JP
BOULLAIS, C
BEAUCOURT, JP
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1989, 27 (04): : 473 - 480
[8] SYNTHESIS OF CHIRAL 12-PHENYL(H-2)DODECANOIC ACIDS - USEFUL METABOLIC PROBES FOR THE BIOSYNTHESIS OF 1-ALKENES FROM FATTY-ACIDS
GORGEN, G
BOLAND, W
PREISS, U
SIMON, H
HELVETICA CHIMICA ACTA, 1989, 72 (05) : 917 - 928
[9] SYNTHESIS OF (8S,9S,11R,12R,15S)-9,11-DIDEOXY-9,11-ETHANOPROSTAGLANDIN-H2
VALEEV, FA
GAISINA, IN
MIFTAKHOV, MS
TOLSTIKOV, GA
ZHURNAL ORGANICHESKOI KHIMII, 1993, 29 (08): : 1630 - 1632
[10] BIOSYNTHESIS OF VITAMIN-B12 - INCORPORATION OF (11S)-[11-H-2]-PORPHOBILINOGEN, AND (11R)-[11-H-2]PORPHOBILINOGEN INTO SIROHYDROCHLORIN AND 2,7,20-TRIMETHYLISOBACTERIOCHLORIN
WEAVER, GW
BLANCHE, F
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DEBUSSCHE, L
LEEPER, FJ
BATTERSBY, AR
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) : 1125 - 1127

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