Synthesis of a α-C-mannosyltryptophan derivative, naturally occurring C-glycosyl amino acid found in human ribonuclease

Synlett

Volumn , Issue 1, 1999, Pages 123-125

  Nishikawa, Toshio ^a   Ishikawa, Miyuki ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

C glycosidation; Indole synthesis; Mannose; Tinacetylene; Tryptophan

Indexed keywords

INDOLE DERIVATIVE; MANNOSE; RIBONUCLEASE; TRYPTOPHAN DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CARBOHYDRATE ANALYSIS; CELL INTERACTION; GLYCOPROTEIN SYNTHESIS; IMMUNE RESPONSE; MOLECULAR INTERACTION; PROTEIN STABILITY;

EID: 0032911810     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3154     Document Type: Article

References (31)

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24. We have synthesized about 4 g of the compound 5.
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28. Diastereoisomeric mixture 10 was separated by silica gel TLC.
29. 3), 4.20 (1H, dd, J = 12, 3.5 Hz, H-6), 4.72 (1H, dd, J = 12, 8 Hz, H-6), 4.78 (1H, q, J = 7 Hz, CH-NHAc), 5.19 (1H, dd, J = 6.5, 4.5 Hz, H-4), 5.34 (1H, d, J = 6.5 Hz, H-1), 5.36 (1H, dd, J = 6.5, 3 Hz, H-3), 5.71 (1H, dd, J = 6.5, 3 Hz, H-2), 6.32 (1H, br d, J = 7.5 Hz, NHAc), 7.12 (1H, td, J = 7.5, 1 Hz, H-5′), 7.21 (1H, td, J = 7.5, 1 Hz, H-6′), 7.36 (1H, br d, J = 8 Hz, H-7′), 7.53 (1H, br d, J = 7.5 Hz, H-4′), 8.46 (1H, br s, NH of indole).
30. 1H-NMR spectrum of 9 as a diastereo mixture was difficult to assign, we identified two signal peaks (δ = 5.15, 5.08 ppm) for proton of C-1 position.
31. 4 conformation of the mannose moiety in 6.