Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine
Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale as...
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Published in | Journal of organic chemistry Vol. 58; no. 26; pp. 7565 - 7571 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.12.1993
Amer Chemical Soc |
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Abstract | Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1. |
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AbstractList | Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1. |
Author | Russell, K. C Hruby, Victor J Nicolas, Ernesto Knollenberg, J |
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Keywords | ALPHA DESIGN OPTICALLY PURE ISOMERS ANALOGS UNUSUAL AMINO-ACIDS METHYLPHENYLALANINE Michael addition α-Aminoacid Chiral auxiliary Asymmetric synthesis Phenols Benzenic compound Methylation Organic carbamate |
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References | TOMIOKA, K (WOS:A1986AYF2700029) 1986; 27 DALE, JA (WOS:A1969E104100013) 1969; 34 EVANS, DA (WOS:A1990DC94100045) 1990; 112 DHARANIPRAGADA, R (WOS:A1989CE61600012) 1989; 30 NICOLAS, E (WOS:A1989CE61600013) 1989; 30 VISWANATHA V (WOS:A1993MN59700042.21) 1980; 45 HRUBY VJ (WOS:A1993MN59700042.13) 1985 BRANDSTROM, A (WOS:A1974U677400022) 1974; B 28 HRUBY VJ (WOS:A1993MN59700042.12) 1988 EVANS, DA (WOS:A1988M188300037) 1988; 110 WILLIAMS RM (WOS:A1993MN59700042.22) 1989; 7 CARON, M (WOS:A1988Q731200063) 1988; 53 DHARANIPRAGADA, R (WOS:A1992HX16200006) 1992; 48 HRUBY, VJ (WOS:A1991FR69000010) 1991; 34 KATAOKA, Y (WOS:A1976BQ89400049) 1976; 49 KAZMIERSKI, W (WOS:A1988M440600005) 1988; 44 NICOLAS, E (WOS:A1993KK26300039) 1993; 58 MELNYK, O (WOS:A1992HC16500007) 1992; 48 HRUBY, VJ (WOS:A1990DH98200001) 1990; 268 HRUBY VJ (WOS:A1993MN59700042.10) 1989 DHARANIPRAGADA, R (WOS:A1992JG48500028) 1992; 48 TOTH, G (WOS:A1992JB46300006) 1992; 35 |
References_xml | – volume: 268 start-page: 249 year: 1990 ident: WOS:A1990DH98200001 article-title: EMERGING APPROACHES IN THE MOLECULAR DESIGN OF RECEPTOR-SELECTIVE PEPTIDE LIGANDS - CONFORMATIONAL, TOPOGRAPHICAL AND DYNAMIC CONSIDERATIONS publication-title: BIOCHEMICAL JOURNAL contributor: fullname: HRUBY, VJ – volume: 34 start-page: 2543 year: 1969 ident: WOS:A1969E104100013 article-title: ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: DALE, JA – volume: 30 start-page: 6845 year: 1989 ident: WOS:A1989CE61600013 article-title: ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLTYROSINE publication-title: TETRAHEDRON LETTERS contributor: fullname: NICOLAS, E – volume: 49 start-page: 1081 year: 1976 ident: WOS:A1976BQ89400049 article-title: STUDIES OF UNUSUAL AMINO-ACIDS AND THEIR PEPTIDES .6. SYNTHESES AND OPTICAL RESOLUTIONS OF BETA-METHYLPHENYLALANINE AND ITS DIPEPTIDE PRESENT IN BOTTROMYCIN publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: KATAOKA, Y – start-page: 601 year: 1988 ident: WOS:A1993MN59700042.12 publication-title: PEPTIDE CHEM 1987 contributor: fullname: HRUBY VJ – volume: 112 start-page: 4011 year: 1990 ident: WOS:A1990DC94100045 article-title: THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: EVANS, DA – volume: 44 start-page: 697 year: 1988 ident: WOS:A1988M440600005 article-title: A NEW APPROACH TO RECEPTOR LIGAND DESIGN - SYNTHESIS AND CONFORMATION OF A NEW CLASS OF POTENT AND HIGHLY SELECTIVE MU-OPIOID ANTAGONISTS UTILIZING TETRAHYDROISOQUINOLINE CARBOXYLIC-ACID publication-title: TETRAHEDRON contributor: fullname: KAZMIERSKI, W – volume: 7 year: 1989 ident: WOS:A1993MN59700042.22 publication-title: ORGANIC CHEM SERIES contributor: fullname: WILLIAMS RM – volume: 48 start-page: 4733 year: 1992 ident: WOS:A1992HX16200006 article-title: ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - AN EFFICIENT SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLPHENYLALANINE publication-title: TETRAHEDRON contributor: fullname: DHARANIPRAGADA, R – start-page: 487 year: 1985 ident: WOS:A1993MN59700042.13 publication-title: PEPTIDES STRUCTURE F contributor: fullname: HRUBY VJ – volume: 110 start-page: 1238 year: 1988 ident: WOS:A1988M188300037 article-title: ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: EVANS, DA – volume: 27 start-page: 369 year: 1986 ident: WOS:A1986AYF2700029 article-title: ASYMMETRIC CONJUGATE ADDITION-REACTION BY THE USE OF (S)-GAMMA-TRITYLOXYMETHYL-GAMMA-BUTYROLACTAM AS A CHIRAL AUXILIARY publication-title: TETRAHEDRON LETTERS contributor: fullname: TOMIOKA, K – volume: 58 start-page: 766 year: 1993 ident: WOS:A1993KK26300039 article-title: ASYMMETRIC 1,4-ADDITION OF ORGANOCUPRATES TO CHIRAL ALPHA,BETA-UNSATURATED N-ACYL-4-PHENYL-2-OXAZOLIDINONES - A NEW APPROACH TO THE SYNTHESIS OF CHIRAL BETA-BRANCHED CARBOXYLIC-ACIDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: NICOLAS, E – start-page: 405 year: 1989 ident: WOS:A1993MN59700042.10 publication-title: COMPUTER AIDED DRUG contributor: fullname: HRUBY VJ – volume: B 28 start-page: 699 year: 1974 ident: WOS:A1974U677400022 article-title: USE OF TETRABUTYLAMMONIUM AZIDE IN CURTIUS REARRANGEMENT publication-title: ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY contributor: fullname: BRANDSTROM, A – volume: 34 start-page: 1823 year: 1991 ident: WOS:A1991FR69000010 article-title: TOPOGRAPHICALLY DESIGNED ANALOGS OF [D-PEN,D-PEN5]ENKEPHALIN publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: HRUBY, VJ – volume: 48 start-page: 1239 year: 1992 ident: WOS:A1992JG48500028 article-title: THE ABSOLUTE-CONFIGURATION OF AN INTERMEDIATE IN THE ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS publication-title: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS contributor: fullname: DHARANIPRAGADA, R – volume: 35 start-page: 2384 year: 1992 ident: WOS:A1992JB46300006 article-title: RING SUBSTITUTED AND OTHER CONFORMATIONALLY CONSTRAINED TYROSINE ANALOGS OF [D-PEN(2),D-PEN(5)]ENKEPHALIN WITH DELTA-OPIOID RECEPTOR SELECTIVITY publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: TOTH, G – volume: 48 start-page: 841 year: 1992 ident: WOS:A1992HC16500007 article-title: DIASTEREOSELECTIVE ADDITIONS OF ALKYLCUPRATES, ALKENYLCUPRATES, ARYLCUPRATES AND ALLYLCUPRATES TO UNSATURATED CHIRAL IMIDES publication-title: TETRAHEDRON contributor: fullname: MELNYK, O – volume: 45 start-page: 2011 year: 1980 ident: WOS:A1993MN59700042.21 publication-title: J ORG CHEM contributor: fullname: VISWANATHA V – volume: 30 start-page: 6841 year: 1989 ident: WOS:A1989CE61600012 article-title: ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLPHENYLALANINE publication-title: TETRAHEDRON LETTERS contributor: fullname: DHARANIPRAGADA, R – volume: 53 start-page: 5185 year: 1988 ident: WOS:A1988Q731200063 article-title: REGIOSELECTIVE AZIDE OPENING OF 2,3-EPOXY ALCOHOLS BY [TI(O-I-PR)2(N3)2] - SYNTHESIS OF ALPHA-AMINO-ACIDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CARON, M |
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Snippet | Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the... |
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SubjectTerms | Chemistry Chemistry, Organic Exact sciences and technology Noncondensed benzenic compounds Organic chemistry Physical Sciences Preparations and properties Science & Technology |
Title | Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine |
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