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Volumn 131, Issue 15, 2009, Pages 5438-5443

Toward homogeneous erythropoietin: Chemical synthesis of the Ala 1-Gly 28 glycopeptide domain by "Alanine" ligation

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID PEPTIDES; CHEMICAL SYNTHESIS; DIRECT COUPLING; FUNCTIONALIZATION; GLYCOFORM; GLYCOPEPTIDE; N-LINKED; N-TERMINAL; NATIVE CHEMICAL LIGATION; THIOESTER;

EID: 67849097425     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808707w     Document Type: Article
Times cited : (46)

References (58)
  • 13
    • 67849092356 scopus 로고    scopus 로고
    • For general reviews on EPO, see: a, Wiley-VCH Verlag GmbH and Co. KGaA: Weinheim
    • For general reviews on EPO, see: (a) Sytkowski, A. J. Erythropoietin; Wiley-VCH Verlag GmbH and Co. KGaA: Weinheim, 2004.
    • (2004) Erythropoietin
    • Sytkowski, A.J.1
  • 20
    • 0036462601 scopus 로고    scopus 로고
    • (b) Roth, J. Chem Rev. 2002, 102, 285-303.
    • (2002) Chem Rev , vol.102 , pp. 285-303
    • Roth, J.1
  • 24
    • 34248230589 scopus 로고    scopus 로고
    • For recent examples of protein synthesis using NCL, see: b
    • For recent examples of protein synthesis using NCL, see: (b) Torbeev, V. Y.; Kent, S. B. H. Angew. Chem., Int. Ed. 2007, 46, 1667-1670.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 1667-1670
    • Torbeev, V.Y.1    Kent, S.B.H.2
  • 26
  • 27
    • 40149092211 scopus 로고    scopus 로고
    • Note that the sialyloligosaccharide was isolated from hen's egg yolk and does not contain any fucose unit. See
    • Note that the sialyloligosaccharide was isolated from hen's egg yolk and does not contain any fucose unit. See: Yamamoto, N.; Tanabe, Y.; Okamoto, R.; Dawson, P. E.; Kajihara, Y. J. Am. Chem. Soc. 2008, 130, 501-510.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 501-510
    • Yamamoto, N.1    Tanabe, Y.2    Okamoto, R.3    Dawson, P.E.4    Kajihara, Y.5
  • 28
    • 0019529504 scopus 로고
    • For other direct condensation methods, see: a
    • For other direct condensation methods, see: (a) Blake, J. Int. J. Pept. Protein Res. 1981, 17, 273-274.
    • (1981) Int. J. Pept. Protein Res , vol.17 , pp. 273-274
    • Blake, J.1
  • 30
  • 33
    • 0030037155 scopus 로고    scopus 로고
    • For other examples of auxiliary-based cysteine-free ligations, see: a
    • For other examples of auxiliary-based cysteine-free ligations, see: (a) Canne, L. E.; Bark, S. J.; Kent, S. B. H. J. Am. Chem. Soc. 1996, 118, 5891-5896.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 5891-5896
    • Canne, L.E.1    Bark, S.J.2    Kent, S.B.H.3
  • 41
    • 0035977638 scopus 로고    scopus 로고
    • For other studies on alanine ligations, see: a
    • For other studies on alanine ligations, see: (a) Yan, L. Z.; Dawson, P. E. J. Am. Chem. Soc. 2001, 123, 526-533,
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 526-533
    • Yan, L.Z.1    Dawson, P.E.2
  • 42
    • 33847791752 scopus 로고    scopus 로고
    • and references therein. (b) Pentelute, B.; Kent, S. B. H. Org. Lett. 2007, 9, 687-690.
    • and references therein. (b) Pentelute, B.; Kent, S. B. H. Org. Lett. 2007, 9, 687-690.
  • 44
    • 52449084906 scopus 로고    scopus 로고
    • For other studies on valine ligations, see
    • For other studies on valine ligations, see: Haase, C.; Rohde, H.; Seitz, O. Angew. Chem., Int. Ed. 2008, 47, 6807-6810.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 6807-6810
    • Haase, C.1    Rohde, H.2    Seitz, O.3
  • 46
    • 67849128630 scopus 로고    scopus 로고
    • For other studies on homocysteine ligations, see
    • For other studies on homocysteine ligations, see: Tam, J. P.; Yu, Q. Biopolymers 1998, 46, 5402-5406.
    • (1998) Biopolymers , vol.46 , pp. 5402-5406
    • Tam, J.P.1    Yu, Q.2
  • 47
    • 67849111478 scopus 로고    scopus 로고
    • In addition to alanine, valine, and homocysteine ligations, a phenylalanine ligation has also been reported. See: (a) Botti, P, Tchertchian, S. WO 133962, 2006
    • In addition to alanine, valine, and homocysteine ligations, a phenylalanine ligation has also been reported. See: (a) Botti, P.; Tchertchian, S. WO 133962, 2006.
  • 49
    • 67849104564 scopus 로고    scopus 로고
    • Following completion of our studies, C.-H. Wong and co-workers published a direct aminolysis method that could, in theory, be applied to the synthesis of our glycopeptide fragment. See ref 11d
    • Following completion of our studies, C.-H. Wong and co-workers published a direct aminolysis method that could, in theory, be applied to the synthesis of our glycopeptide fragment. See ref 11d.
  • 51
    • 84869564899 scopus 로고    scopus 로고
    • Mepro)-OH) to avoid unwanted aspartimide formation.
    • Mepro)-OH) to avoid unwanted aspartimide formation.
  • 54
    • 84869578811 scopus 로고    scopus 로고
    • 19 has not epimerized, model studies with the corresponding disaccharide substrates indicate formation of a separable mixture of diastereomers in a 4:1 ratio.
    • 19 has not epimerized, model studies with the corresponding disaccharide substrates indicate formation of a separable mixture of diastereomers in a 4:1 ratio.
  • 56
    • 67849130488 scopus 로고    scopus 로고
    • Peptide 19 was prepared in two steps from 33, see the Supporting Information for synthesis.
    • Peptide 19 was prepared in two steps from 33, see the Supporting Information for synthesis.
  • 57
    • 33746299267 scopus 로고    scopus 로고
    • Other examples of competitive intramolecular NCL have been observed. See: a
    • Other examples of competitive intramolecular NCL have been observed. See: (a) Bang, D.; Pentelute, B. L.; Kent, S. B. H. Angew. Chem., Int. Ed. 2006, 45, 3985-3988.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 3985-3988
    • Bang, D.1    Pentelute, B.L.2    Kent, S.B.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.