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Volumn 2, Issue 1, 2007, Pages 114-122

Malyngamide X: The first (7R)-lyngbic acid that connects to a new tripeptide backbone from the Thai sea hare Bursatella leachii

Author keywords

Chiral resolution; Chiral solvating agent; Malyngamide X; Natural products; Sea hare

Indexed keywords

ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; MALYNGAMIDE X; OLIGOPEPTIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

EID: 33846279757     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600219     Document Type: Article
Times cited : (42)

References (48)
  • 4
    • 0001177687 scopus 로고    scopus 로고
    • Compound 3 is the major fatty acid substructure in malyngamides; for a review, see reference [1]; a L. T. Tan, T. Okino, W. H. Gerwick, J. Nat. Prod. 2000, 63, 952-955;
    • Compound 3 is the major fatty acid substructure in malyngamides; for a review, see reference [1]; a) L. T. Tan, T. Okino, W. H. Gerwick, J. Nat. Prod. 2000, 63, 952-955;
  • 13
    • 0022573266 scopus 로고    scopus 로고
    • The tripeptide moiety 1 was numbered with respect to the neurotoxin janolusimide (6), a very similar tripeptide; a) G. Sodano, A. Spinella, Tetrahedron Lett. 1986, 27, 2505-2508;
    • The tripeptide moiety 1 was numbered with respect to the neurotoxin janolusimide (6), a very similar tripeptide; a) G. Sodano, A. Spinella, Tetrahedron Lett. 1986, 27, 2505-2508;
  • 18
    • 0033558171 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 448-476.
    • (1999) Chem. Int. Ed , vol.38 , pp. 448-476
    • Angew1
  • 19
    • 0001246453 scopus 로고    scopus 로고
    • 3- pyrrolin-2-one, see: B. J. L. Royles, Chem. Rev. 1995, 95, 1981-2001.
    • 3- pyrrolin-2-one, see: B. J. L. Royles, Chem. Rev. 1995, 95, 1981-2001.
  • 20
    • 0000253239 scopus 로고    scopus 로고
    • H,H = 0-4 Hz); a) C. H. Heathcock, M. C. Pirrung, J. E. Sohn, J. Org. Chem. 1979, 44, 4294-4299;
    • H,H = 0-4 Hz); a) C. H. Heathcock, M. C. Pirrung, J. E. Sohn, J. Org. Chem. 1979, 44, 4294-4299;
  • 22
    • 0033525048 scopus 로고    scopus 로고
    • H,H is a value typical for an anti configuration, the NOE analysis should be reliable, as no significant conformational change takes place; N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866-876. (Chemical Equation Presented)
    • H,H is a value typical for an anti configuration, the NOE analysis should be reliable, as no significant conformational change takes place; N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866-876. (Chemical Equation Presented)
  • 24
    • 0001123933 scopus 로고    scopus 로고
    • The method pioneered by Pirkle and Beare follows from the possibility of relating the sense of chemical shift nonequivalence (upfield vs. downfield of a signal) for one enantiomer of a compound dissolved in an optically active solvent; see, for instance: a) W. H. Pirkle, S. D. Beare, J. Am. Chem. Soc. 1969, 91, 5150-5155;
    • The method pioneered by Pirkle and Beare follows from the possibility of relating the sense of chemical shift nonequivalence (upfield vs. downfield of a signal) for one enantiomer of a compound dissolved in an optically active solvent; see, for instance: a) W. H. Pirkle, S. D. Beare, J. Am. Chem. Soc. 1969, 91, 5150-5155;
  • 26
    • 0000237404 scopus 로고
    • c) D. Parker, Chem. Rev. 1991, 91, 1441-1457;
    • (1991) Chem. Rev , vol.91 , pp. 1441-1457
    • Parker, D.1
  • 28
    • 0347520940 scopus 로고    scopus 로고
    • There are very few reports about the use of CSAs for absolute configuration assignment; a S. Latypov, X. Franck, J.-C. Jullian, R. Hocquemiller, B. Figadére, Chem. Eur. J. 2002, 8, 5662-5666;
    • There are very few reports about the use of CSAs for absolute configuration assignment; a) S. Latypov, X. Franck, J.-C. Jullian, R. Hocquemiller, B. Figadére, Chem. Eur. J. 2002, 8, 5662-5666;
  • 31
    • 33846322662 scopus 로고    scopus 로고
    • The interaction between TFAE and the substrate was not as strong as the covalent bond of the MTPA ester in the modified Mosher method. The observed ΔδRS values were thus the average shifts of the signals of the diastereomeric complexes that rapidly equilibrate with the bulk of cosolvent on the NMR timescale
    • RS values were thus the average shifts of the signals of the diastereomeric complexes that rapidly equilibrate with the bulk of cosolvent on the NMR timescale.
  • 33
    • 33846282022 scopus 로고
    • For absolute configuration assignment with aid from conformational calculations, see, for example: a
    • For absolute configuration assignment with aid from conformational calculations, see, for example: a) M. Ubutaka, X.-C. Cheng, M. Isobe, K. Isono, J. Chem. Soc. Perkin Trans. 1 1993, 617-624;
    • (1993) J. Chem. Soc. Perkin Trans. 1 , pp. 617-624
    • Ubutaka, M.1    Cheng, X.-C.2    Isobe, M.3    Isono, K.4
  • 37
    • 33846321979 scopus 로고    scopus 로고
    • 3 and 8-H.
    • 3 and 8-H.
  • 38
    • 0031909145 scopus 로고    scopus 로고
    • The biosynthetic considerations have recently been employed to solve the stereochemistry of C7′; see: Y. Kan, T. Fujita, H. Nagai, B. Sakamoto, Y. Hokama, J. Nat. Prod. 1998, 61, 152-155, and reference [7].
    • The biosynthetic considerations have recently been employed to solve the stereochemistry of C7′; see: Y. Kan, T. Fujita, H. Nagai, B. Sakamoto, Y. Hokama, J. Nat. Prod. 1998, 61, 152-155, and reference [7].
  • 39
    • 33846282120 scopus 로고    scopus 로고
    • We recently completed the total synthesis of (7′R)-1. The specific rotation of natural 1, α]D, 6.2 (c, 0.8, MeOH, matched that of (7′R)-1, α]D, 5.9 (c, 0.8, MeOH, but differed from that of (7′S)-1, α]D, 15.4 (c, 0.8, MeOH, This difference must be due to the large distance between the C7′ stereogenic center and the other five stereogenic centers in the tripeptide portion. The consistent result in the NMR chiral solvation experiments was obtained with synthetic (7′R)-1. The details for the total synthesis of both (7′R, and (7′S)-malyngamide X and the NMR chiral solvation experiments will be reported elsewhere
    • D = -15.4 (c = 0.8, MeOH). This difference must be due to the large distance between the C7′ stereogenic center and the other five stereogenic centers in the tripeptide portion. The consistent result in the NMR chiral solvation experiments was obtained with synthetic (7′R)-1. The details for the total synthesis of both (7′R)- and (7′S)-malyngamide X and the NMR chiral solvation experiments will be reported elsewhere.
  • 42
    • 33846306088 scopus 로고    scopus 로고
    • D measurements.
    • D measurements.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.