Total synthesis of enantiopure β-D-mannosyl phosphomycoketides from Mycobacterium tuberculosis

Journal of the American Chemical Society

Volumn 128, Issue 14, 2006, Pages 4546-4547

  Van Summeren, Ruben P ^a   Moody, D Branch ^b   Feringa, Ben L ^a   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA DEXTRO MANNOSYL PHOSPHOMYCOKETIDE DERIVATIVE; ISOPRENOID; MYCOBACTERIUM ANTIGEN; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; MYCOBACTERIUM TUBERCULOSIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; FATTY ALCOHOLS; MANNOSE; MYCOBACTERIUM TUBERCULOSIS; PHOSPHORIC ACID ESTERS; STEREOISOMERISM;

EID: 33646049727     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060499i     Document Type: Article

References (15)

1. Moody, D. B.; Ulrichs, T.; Mühlecker W.; Young, D. C.; Gurcha, S. S.; Grant, E.; Rosat, J.-P.; Brenner, M. B.; Costello, C. E.; Besra, G. S.; Porcelli, S. A. Nature 2000, 404, 884-888.
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15. The anomeric configuration of (all-S)-1 was unequivocally determined by NOE correlation between the anomeric hydrogen and H's 3 and 5 of the sugar moiety and by a cross-ring fragmentation (m/z. 587.5) and a dehydration (m/z 689.5) in the low-energy ESI CID spectrum. Additional support was given by comparison of the chemical shift of the anomeric proton of 1 with that of the anomeric proton of the independently synthesized (all-S)-α-1 analogue as well as by comparison of the VCH coupling of both anomers (α = 169 Hz, β= 159 Hz). (16) Bioassays were conducted at the Brighamand Women's Hospital, Harvard Medical School. Details will be reported in due course.