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Volumn 125, Issue 5, 2003, Pages 1278-1283

Detection and amplification of a small enantiomeric imbalance in α-amino acids by a helical poly(phenylacetylene) with crown ether pendants

Author keywords

[No Author keywords available]

Indexed keywords

CIRCULAR DICHROISM;

EID: 0037419845     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028348c     Document Type: Article
Times cited : (206)

References (97)
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    • note
    • We measured the viscosity of poly-1 with or without L-Ala to investigate a change in rigidity of the polymer upon complexation with L-Ala. Poly-1 showed a linear relationship in the Huggins plot, and the intrinsic viscosity was estimated to be 2.00 dL/g. However, in the presence of L-Ala, the intrinsic viscosity increased to 3.56, which was 1.8 times larger than that of the poly-1. Under the present experimental conditions, the poly-1 solutions containing L-Ala showed a full ICD at 25 °C. These results suggest that poly-1 becomes more stiff than the poly-1 upon complexation with L-Ala (see Supporting Information).
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    • For recent examples of chirality recognition of protected amino acids in organic media, see: (a) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (b) Zahn, S.; Canary, J. W. Org. Lett. 1999, 1, 861-864. (c) Mizutani, T.; Sakai, N.; Yagi, S.; Takagishi, T.; Kitagawa, S.; Ogoshi, H. J. Am. Chem. Soc. 2000, 122, 748-749. (d) Shinkai, S.; Ikeda, M.; Sugasaki, A.; Takeuchi, M. Acc. Chem. Res. 2001, 34, 494-503. (e) Canary, J. W.; Holmes, A. E.; Liu, J. Enantiomer 2001, 6, 181-188. For recent examples of chiral or chirality recognition of free amino acids, see ref 9 and: (f) Tsukube, H.; Shinoda, S.; Uenishi, J.; Kanatani, T.; Itoh, H.; Shiode, M.; Iwachido, T.; Yonemitsu, O. Inorg, Chem. 1998, 37, 1585-1591. (g) Leipert, D.; Nopper, D.; Bauser, M.; Gauglitz, G.; Jung, G. Angew. Chem., Int. Ed. 1999, 38, 3308-3311.
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    • Tsukube, H.1    Shinoda, S.2    Uenishi, J.3    Kanatani, T.4    Itoh, H.5    Shiode, M.6    Iwachido, T.7    Yonemitsu, O.8
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    • 0012982202 scopus 로고    scopus 로고
    • For recent examples of chirality recognition of protected amino acids in organic media, see: (a) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (b) Zahn, S.; Canary, J. W. Org. Lett. 1999, 1, 861-864. (c) Mizutani, T.; Sakai, N.; Yagi, S.; Takagishi, T.; Kitagawa, S.; Ogoshi, H. J. Am. Chem. Soc. 2000, 122, 748-749. (d) Shinkai, S.; Ikeda, M.; Sugasaki, A.; Takeuchi, M. Acc. Chem. Res. 2001, 34, 494-503. (e) Canary, J. W.; Holmes, A. E.; Liu, J. Enantiomer 2001, 6, 181-188. For recent examples of chiral or chirality recognition of free amino acids, see ref 9 and: (f) Tsukube, H.; Shinoda, S.; Uenishi, J.; Kanatani, T.; Itoh, H.; Shiode, M.; Iwachido, T.; Yonemitsu, O. Inorg, Chem. 1998, 37, 1585-1591. (g) Leipert, D.; Nopper, D.; Bauser, M.; Gauglitz, G.; Jung, G. Angew. Chem., Int. Ed. 1999, 38, 3308-3311.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 3308-3311
    • Leipert, D.1    Nopper, D.2    Bauser, M.3    Gauglitz, G.4    Jung, G.5


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