The stereoselective construction of E- and Z-Delta-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain

The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate.

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Published inChemical communications (Cambridge, England) Vol. 52; no. 7; pp. 1478 - 1481
Main Authors Yasuno, Yoko, Nishimura, Akito, Yasukawa, Yoshifumi, Karita, Yuma, Ohfune, Yasufumi, Shinada, Tetsuro
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.01.2016
Subjects
Amino Acids - chemistry
Chemistry
Chemistry, Multidisciplinary
Esters - chemistry
Mycotoxins - chemical synthesis
Mycotoxins - chemistry
Oligopeptides - chemical synthesis
Physical Sciences
Proton Magnetic Resonance Spectroscopy
Science & Technology
ELUCIDATION
CHEMICAL BIOLOGY
PEPTIDES
AMINO-ACIDS
NATURAL-PRODUCTS
CONFIGURATION
LEPTOSTROMIFORMIS
IDENTIFICATION
DERIVATIVES
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Abstract The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate.
AbstractList The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy)carbonyl)amino)-2-(diphenoxyphosphoryl)acetate as a common synthetic precursor for the synthesis of E -Δ-dehydroisoleucine and E -Δ-aspartate.
The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy)carbonyl)amino)-2-(diphenoxyphosphoryl)acetate as a common synthetic precursor for the synthesis of E-Δ-dehydroisoleucine and E-Δ-aspartate.
The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate.
Author Shinada, Tetsuro
Yasukawa, Yoshifumi
Nishimura, Akito
Karita, Yuma
Yasuno, Yoko
Ohfune, Yasufumi
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Cites_doi 10.1246/bcsj.77.2219
10.1016/j.tetasy.2005.05.023
10.1021/jacs.5b05550
10.1002/ejoc.201300112
10.1021/ja049499d
10.1002/anie.200702537
10.1021/ja401457h
10.1021/ol5018933
10.1246/cl.2012.658
10.1039/c3np70103d
10.1016/j.tet.2015.06.001
10.1007/s00726-014-1846-4
10.1021/ol201307y
10.1016/j.tetlet.2009.09.072
10.1021/ja511872a
10.1007/s00726-009-0466-x
10.1038/NCHEMBIO.1199
10.1021/cr950005s
10.1246/bcsj.73.1605
10.1021/ja991037q
10.1071/BI9770269
10.1016/0006-2952(87)90141-9
10.1038/nchembio.1199
10.1055/s-1992-26143
10.1021/jo00068a047
10.1016/S0040-4039(00)79004-6
10.1002/ejoc.200800602
10.1016/S0040-4020(01)83436-0
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Issue 7
Keywords ELUCIDATION
CHEMICAL BIOLOGY
PEPTIDES
AMINO-ACIDS
NATURAL-PRODUCTS
CONFIGURATION
LEPTOSTROMIFORMIS
IDENTIFICATION
DERIVATIVES
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References Jiang, JT (WOS:000359033700001) 2015; 71
CULVENOR, CCJ (WOS:A1977EA85700001) 1977; 30
Shangguan, N (WOS:000271603000003) 2009; 50
Ueda, M (WOS:000307862300001) 2012; 41
Grimley, JS (WOS:000250966100008) 2007; 46
SCHMIDT, U (WOS:A1992HU46200019) 1992
Yasuno, Y (WOS:000316389800007) 2013; 2013
LACEY, E (WOS:A1987J045800013) 1987; 36
Kuranaga, T (WOS:000358896600040) 2015; 137
Kuranaga, T (WOS:000333040900011) 2014; 31
Molinaro, C (WOS:000348483400070) 2015; 137
Kuranaga, T (WOS:000317548400049) 2013; 135
COMBS, AP (WOS:A1992JU94000005) 1992; 33
Krasovskiy, A (WOS:000293252800014) 2011; 13
Nagano, T (WOS:000088837000020) 2000; 73
Stohlmeyer, MM (WOS:000081216800043) 1999; 121
Schenone, M (WOS:000317025800011) 2013; 9
Ma, ZW (WOS:000339982300050) 2014; 16
CULVENOR, CCJ (WOS:A1989U178100009) 1989; 45
Humphrey, JM (WOS:A1997XZ27000010) 1997; 97
Shiraishi, Y (WOS:000226192600014) 2004; 77
Chandrasekhar, S (WOS:000230879800003) 2005; 16
Ferreira, PMT (WOS:000279190400020) 2010; 39
Roff, GJ (WOS:000220637100024) 2004; 126
Siodlak, D (WOS:000347248500001) 2015; 47
COLEMAN, RS (WOS:A1993LV42500047) 1993; 58
Kuranaga (C5CC08458J-(cit10b)/*[position()=1]) 2014; 31
Roff (C5CC08458J-(cit16b)/*[position()=1]) 2004; 126
Ferreira (C5CC08458J-(cit16d)/*[position()=1]) 2010; 39
Kuranaga (C5CC08458J-(cit10c)/*[position()=1]) 2015; 137
Siodłak (C5CC08458J-(cit18a)/*[position()=1]) 2015; 47
Molinaro (C5CC08458J-(cit12)/*[position()=2]) 2015; 137
Stohlmeyer (C5CC08458J-(cit6)/*[position()=1]) 1999; 121
Ma (C5CC08458J-(cit11)/*[position()=1]) 2014; 16
Yasuno (C5CC08458J-(cit13)/*[position()=1]) 2013
Combs (C5CC08458J-(cit16a)/*[position()=1]) 1992; 33
Kuranaga (C5CC08458J-(cit10a)/*[position()=1]) 2013; 135
Schenone (C5CC08458J-(cit19b)/*[position()=1]) 2013; 9
Lacey (C5CC08458J-(cit2)/*[position()=1]) 1987; 36
Culvenor (C5CC08458J-(cit1a)/*[position()=1]) 1977; 30
Coleman (C5CC08458J-(cit14)/*[position()=1]) 1993; 58
Culvenor (C5CC08458J-(cit1b)/*[position()=1]) 1989; 45
Nagano (C5CC08458J-(cit9a)/*[position()=1]) 2000; 73
Chandrasekhar (C5CC08458J-(cit4)/*[position()=1]) 2005; 16
Shangguan (C5CC08458J-(cit5)/*[position()=1]) 2009; 50
Humphrey (C5CC08458J-(cit7)/*[position()=1]) 1997; 97
Ueda (C5CC08458J-(cit19a)/*[position()=1]) 2012; 41
Ferreira (C5CC08458J-(cit16c)/*[position()=1]) 2008
Grimley (C5CC08458J-(cit3)/*[position()=1]) 2007; 46
Shiraishi (C5CC08458J-(cit9b)/*[position()=1]) 2004; 77
Schmidt (C5CC08458J-(cit8)/*[position()=1]) 1992
Krasovskiy (C5CC08458J-(cit15)/*[position()=1]) 2011; 13
Jiang (C5CC08458J-(cit18b)/*[position()=1]) 2015; 71
References_xml – volume: 33
  start-page: 6419
  year: 1992
  ident: WOS:A1992JU94000005
  article-title: CHARACTERIZATION OF ALPHA-HALO-IMINE INTERMEDIATES DERIVED FROM HALOGENATION OF DEHYDROAMINO ACID-DERIVATIVES
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: COMBS, AP
– volume: 77
  start-page: 2219
  year: 2004
  ident: WOS:000226192600014
  article-title: A new synthetic method for dipeptides containing alpha,beta-didehydroamino acids utilizing an alpha-tosylglycine residue
  publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
  doi: 10.1246/bcsj.77.2219
  contributor:
    fullname: Shiraishi, Y
– volume: 16
  start-page: 2209
  year: 2005
  ident: WOS:000230879800003
  article-title: The first simple and efficient synthesis of the unusual dipeptide part of Phomopsin A
  publication-title: TETRAHEDRON-ASYMMETRY
  doi: 10.1016/j.tetasy.2005.05.023
  contributor:
    fullname: Chandrasekhar, S
– volume: 137
  start-page: 9443
  year: 2015
  ident: WOS:000358896600040
  article-title: Elucidation and Total Synthesis of the Correct Structures of Tridecapeptides Yaku'amides A and B. Synthesis-Driven Stereochemical Reassignment of Four Amino Acid Residues
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.5b05550
  contributor:
    fullname: Kuranaga, T
– volume: 2013
  start-page: 1884
  year: 2013
  ident: WOS:000316389800007
  article-title: Stereoselective Synthesis of (E)-alpha,beta-Dehydroamino Acid Esters
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.201300112
  contributor:
    fullname: Yasuno, Y
– volume: 126
  start-page: 4098
  year: 2004
  ident: WOS:000220637100024
  article-title: A versatile chemo-enzymatic route to enantiomerically pure beta-branched alpha-amino acids
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja049499d
  contributor:
    fullname: Roff, GJ
– volume: 46
  start-page: 8157
  year: 2007
  ident: WOS:000250966100008
  article-title: The enantioselective synthesis of phomopsin b
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200702537
  contributor:
    fullname: Grimley, JS
– volume: 135
  start-page: 5467
  year: 2013
  ident: WOS:000317548400049
  article-title: Total Synthesis and Complete Structural Assignment of Yaku'amide A
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja401457h
  contributor:
    fullname: Kuranaga, T
– volume: 16
  start-page: 4044
  year: 2014
  ident: WOS:000339982300050
  article-title: Selective Access to E- and Z-Delta Ile-Containing Peptides via a Stereospecific E2 Dehydration and an O -> N Acyl Transfer
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol5018933
  contributor:
    fullname: Ma, ZW
– volume: 41
  start-page: 658
  year: 2012
  ident: WOS:000307862300001
  article-title: Chemical Biology of Natural Products on the Basis of Identification of Target Proteins
  publication-title: CHEMISTRY LETTERS
  doi: 10.1246/cl.2012.658
  contributor:
    fullname: Ueda, M
– volume: 31
  start-page: 514
  year: 2014
  ident: WOS:000333040900011
  article-title: Cu-mediated enamide formation in the total synthesis of complex peptide natural products
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/c3np70103d
  contributor:
    fullname: Kuranaga, T
– volume: 36
  start-page: 2133
  year: 1987
  ident: WOS:A1987J045800013
  article-title: INTERACTION OF PHOMOPSIN-A AND RELATED-COMPOUNDS WITH PURIFIED SHEEP BRAIN TUBULIN
  publication-title: BIOCHEMICAL PHARMACOLOGY
  contributor:
    fullname: LACEY, E
– volume: 30
  start-page: 269
  year: 1977
  ident: WOS:A1977EA85700001
  article-title: ISOLATION OF TOXIC METABOLITES OF PHOMOPSIS-LEPTOSTROMIFORMIS RESPONSIBLE FOR LUPINOSIS
  publication-title: AUSTRALIAN JOURNAL OF BIOLOGICAL SCIENCES
  contributor:
    fullname: CULVENOR, CCJ
– volume: 71
  start-page: 5431
  year: 2015
  ident: WOS:000359033700001
  article-title: Bulky alpha,beta-dehydroamino acids: their occurrence in nature, synthesis, and applications
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2015.06.001
  contributor:
    fullname: Jiang, JT
– volume: 58
  start-page: 4452
  year: 1993
  ident: WOS:A1993LV42500047
  article-title: STEREOSELECTIVE BROMINATION OF DEHYDROAMINO ACIDS WITH CONTROLLABLE RETENTION OR INVERSION OF OLEFIN CONFIGURATION
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: COLEMAN, RS
– volume: 47
  start-page: 1
  year: 2015
  ident: WOS:000347248500001
  article-title: alpha,beta-Dehydroamino acids in naturally occurring peptides
  publication-title: AMINO ACIDS
  doi: 10.1007/s00726-014-1846-4
  contributor:
    fullname: Siodlak, D
– volume: 13
  start-page: 3822
  year: 2011
  ident: WOS:000293252800014
  article-title: Highly Selective Reactions of Unbiased Alkenyl Halides and Alkylzinc Halides: Negishi-Plus Couplings
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol201307y
  contributor:
    fullname: Krasovskiy, A
– volume: 97
  start-page: 2243
  year: 1997
  ident: WOS:A1997XZ27000010
  article-title: Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides
  publication-title: CHEMICAL REVIEWS
  contributor:
    fullname: Humphrey, JM
– volume: 73
  start-page: 1605
  year: 2000
  ident: WOS:000088837000020
  article-title: A new and convenient method for the synthesis of dehydroamino acids starting from ethyl N-Boc- and N-Z-alpha-tosylglycinates and various nitro compounds
  publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
  contributor:
    fullname: Nagano, T
– volume: 50
  start-page: 6748
  year: 2009
  ident: WOS:000271603000003
  article-title: A copper-carbodiimide approach to the phomopsin tripeptide side chain
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2009.09.072
  contributor:
    fullname: Shangguan, N
– volume: 121
  start-page: 6100
  year: 1999
  ident: WOS:000081216800043
  article-title: A stereospecific elimination to form dehydroamino acids: Synthesis of the phomopsin tripeptide side chain
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: Stohlmeyer, MM
– volume: 137
  start-page: 999
  year: 2015
  ident: WOS:000348483400070
  article-title: Catalytic, Asymmetric, and Stereodivergent Synthesis of Non-Symmetric beta,beta-Diaryl-alpha-Amino Acids
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja511872a
  contributor:
    fullname: Molinaro, C
– volume: 39
  start-page: 499
  year: 2010
  ident: WOS:000279190400020
  article-title: Synthesis and electrochemical behaviour of beta-halodehydroamino acid derivatives
  publication-title: AMINO ACIDS
  doi: 10.1007/s00726-009-0466-x
  contributor:
    fullname: Ferreira, PMT
– volume: 9
  start-page: 232
  year: 2013
  ident: WOS:000317025800011
  article-title: Target identification and mechanism of action in chemical biology and drug discovery
  publication-title: NATURE CHEMICAL BIOLOGY
  doi: 10.1038/NCHEMBIO.1199
  contributor:
    fullname: Schenone, M
– volume: 45
  start-page: 2351
  year: 1989
  ident: WOS:A1989U178100009
  article-title: STRUCTURE ELUCIDATION AND ABSOLUTE-CONFIGURATION OF PHOMOPSIN-A, A HEXAPEPTIDE MYCOTOXIN PRODUCED BY PHOMOPSIS-LEPTOSTROMIFORMIS
  publication-title: TETRAHEDRON
  contributor:
    fullname: CULVENOR, CCJ
– start-page: 487
  year: 1992
  ident: WOS:A1992HU46200019
  article-title: AMINO-ACIDS AND PEPTIDES .81. DIASTEREOSELECTIVE FORMATION OF (Z)-DIDEHYDROAMINO ACID-ESTERS
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: SCHMIDT, U
– volume: 71
  start-page: 5431
  year: 2015
  ident: C5CC08458J-(cit18b)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2015.06.001
  contributor:
    fullname: Jiang
– volume: 97
  start-page: 2243
  year: 1997
  ident: C5CC08458J-(cit7)/*[position()=1]
  publication-title: Chem. Rev.
  doi: 10.1021/cr950005s
  contributor:
    fullname: Humphrey
– volume: 31
  start-page: 514
  year: 2014
  ident: C5CC08458J-(cit10b)/*[position()=1]
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/c3np70103d
  contributor:
    fullname: Kuranaga
– volume: 73
  start-page: 1605
  year: 2000
  ident: C5CC08458J-(cit9a)/*[position()=1]
  publication-title: Bull. Chem. Soc. Jpn.
  doi: 10.1246/bcsj.73.1605
  contributor:
    fullname: Nagano
– volume: 121
  start-page: 6100
  year: 1999
  ident: C5CC08458J-(cit6)/*[position()=1]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja991037q
  contributor:
    fullname: Stohlmeyer
– volume: 30
  start-page: 269
  year: 1977
  ident: C5CC08458J-(cit1a)/*[position()=1]
  publication-title: Aust. J. Biol. Sci.
  doi: 10.1071/BI9770269
  contributor:
    fullname: Culvenor
– volume: 46
  start-page: 8157
  year: 2007
  ident: C5CC08458J-(cit3)/*[position()=1]
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.200702537
  contributor:
    fullname: Grimley
– volume: 50
  start-page: 6748
  year: 2009
  ident: C5CC08458J-(cit5)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2009.09.072
  contributor:
    fullname: Shangguan
– volume: 36
  start-page: 2133
  year: 1987
  ident: C5CC08458J-(cit2)/*[position()=1]
  publication-title: Biochem. Pharmacol.
  doi: 10.1016/0006-2952(87)90141-9
  contributor:
    fullname: Lacey
– volume: 9
  start-page: 232
  year: 2013
  ident: C5CC08458J-(cit19b)/*[position()=1]
  publication-title: Nat. Chem. Biol.
  doi: 10.1038/nchembio.1199
  contributor:
    fullname: Schenone
– volume: 47
  start-page: 1
  year: 2015
  ident: C5CC08458J-(cit18a)/*[position()=1]
  publication-title: Amino Acids
  doi: 10.1007/s00726-014-1846-4
  contributor:
    fullname: Siodłak
– start-page: 1884
  year: 2013
  ident: C5CC08458J-(cit13)/*[position()=1]
  publication-title: Eur. J. Org. Chem.
  doi: 10.1002/ejoc.201300112
  contributor:
    fullname: Yasuno
– start-page: 487
  year: 1992
  ident: C5CC08458J-(cit8)/*[position()=1]
  publication-title: Synthesis
  doi: 10.1055/s-1992-26143
  contributor:
    fullname: Schmidt
– volume: 135
  start-page: 5467
  year: 2013
  ident: C5CC08458J-(cit10a)/*[position()=1]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja401457h
  contributor:
    fullname: Kuranaga
– volume: 137
  start-page: 9443
  year: 2015
  ident: C5CC08458J-(cit10c)/*[position()=1]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/jacs.5b05550
  contributor:
    fullname: Kuranaga
– volume: 16
  start-page: 4044
  year: 2014
  ident: C5CC08458J-(cit11)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol5018933
  contributor:
    fullname: Ma
– volume: 126
  start-page: 4098
  year: 2004
  ident: C5CC08458J-(cit16b)/*[position()=1]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja049499d
  contributor:
    fullname: Roff
– volume: 16
  start-page: 2209
  year: 2005
  ident: C5CC08458J-(cit4)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/j.tetasy.2005.05.023
  contributor:
    fullname: Chandrasekhar
– volume: 39
  start-page: 499
  year: 2010
  ident: C5CC08458J-(cit16d)/*[position()=1]
  publication-title: Amino Acids
  doi: 10.1007/s00726-009-0466-x
  contributor:
    fullname: Ferreira
– volume: 77
  start-page: 2219
  year: 2004
  ident: C5CC08458J-(cit9b)/*[position()=1]
  publication-title: Bull. Chem. Soc. Jpn.
  doi: 10.1246/bcsj.77.2219
  contributor:
    fullname: Shiraishi
– volume: 137
  start-page: 999
  year: 2015
  ident: C5CC08458J-(cit12)/*[position()=2]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja511872a
  contributor:
    fullname: Molinaro
– volume: 41
  start-page: 658
  year: 2012
  ident: C5CC08458J-(cit19a)/*[position()=1]
  publication-title: Chem. Lett.
  doi: 10.1246/cl.2012.658
  contributor:
    fullname: Ueda
– volume: 58
  start-page: 4452
  year: 1993
  ident: C5CC08458J-(cit14)/*[position()=1]
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00068a047
  contributor:
    fullname: Coleman
– volume: 13
  start-page: 3822
  year: 2011
  ident: C5CC08458J-(cit15)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol201307y
  contributor:
    fullname: Krasovskiy
– volume: 33
  start-page: 6419
  year: 1992
  ident: C5CC08458J-(cit16a)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)79004-6
  contributor:
    fullname: Combs
– start-page: 4676
  year: 2008
  ident: C5CC08458J-(cit16c)/*[position()=1]
  publication-title: Eur. J. Org. Chem.
  doi: 10.1002/ejoc.200800602
  contributor:
    fullname: Ferreira
– volume: 45
  start-page: 2351
  year: 1989
  ident: C5CC08458J-(cit1b)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)83436-0
  contributor:
    fullname: Culvenor
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Snippet The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl)...
The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl...
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SubjectTerms Amino Acids - chemistry
Chemistry
Chemistry, Multidisciplinary
Esters - chemistry
Mycotoxins - chemical synthesis
Mycotoxins - chemistry
Oligopeptides - chemical synthesis
Physical Sciences
Proton Magnetic Resonance Spectroscopy
Science & Technology
Title The stereoselective construction of E- and Z-Delta-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain
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