DL-apiose substituted with stable isotopes: synthesis, n.m.r.-spectral analysis, and furanose anomerization.
Publication type: Journal Article
Publication date: 1987-08-01
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
PubMed ID:
3308088
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
The branched-chain pentose DL-apiose has been synthesized in good yield by a new and simple chemical method that can be adapted to prepare (1-13C)-, (2-13C)-, (1-2H)- and/or (2-2H)-enriched derivatives. N.m.r. spectra (1H- and 13C-) have been interpreted with the aid of selective (13C)- and (2H)-enrichment, and 2D and 13C[13C]-n.m.r. spectra. The solution composition of DL-(1-13C)apiose in 2H2O, determined by 13C-n.m.r. spectroscopy, has been found to differ from that determined previously by 1H-n.m.r. spectroscopy. Several 13C-1H and 13C-13C couplings have been measured and interpreted in terms of apiofuranose ring conformation. Ring-opening rate-constants of the four apiofuranoses [3-C-(hydroxymethyl)-alpha- and -beta-D-erythrofuranose, and 3-C-(hydroxymethyl)-alpha- and -beta-L-threofuranose] have been determined by 13C-saturation-transfer n.m.r. spectroscopy, and compared to those obtained previously for the structurally related tetrofuranoses.
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56
Total citations:
56
Citations from 2024:
3
(5.36%)
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GOST
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Snyder J. R. et al. DL-apiose substituted with stable isotopes: synthesis, n.m.r.-spectral analysis, and furanose anomerization. // Carbohydrate Research. 1987. Vol. 166. No. 1. pp. 85-99.
GOST all authors (up to 50)
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Snyder J., Serianni A. S. DL-apiose substituted with stable isotopes: synthesis, n.m.r.-spectral analysis, and furanose anomerization. // Carbohydrate Research. 1987. Vol. 166. No. 1. pp. 85-99.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/0008-6215(87)80046-0
UR - https://doi.org/10.1016/0008-6215(87)80046-0
TI - DL-apiose substituted with stable isotopes: synthesis, n.m.r.-spectral analysis, and furanose anomerization.
T2 - Carbohydrate Research
AU - Snyder, Joseph
AU - Serianni, Anthony S.
PY - 1987
DA - 1987/08/01
PB - Elsevier
SP - 85-99
IS - 1
VL - 166
PMID - 3308088
SN - 0008-6215
SN - 1873-426X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1987_Snyder,
author = {Joseph Snyder and Anthony S. Serianni},
title = {DL-apiose substituted with stable isotopes: synthesis, n.m.r.-spectral analysis, and furanose anomerization.},
journal = {Carbohydrate Research},
year = {1987},
volume = {166},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/0008-6215(87)80046-0},
number = {1},
pages = {85--99},
doi = {10.1016/0008-6215(87)80046-0}
}
Cite this
MLA
Copy
Snyder, Joseph R., et al. “DL-apiose substituted with stable isotopes: synthesis, n.m.r.-spectral analysis, and furanose anomerization..” Carbohydrate Research, vol. 166, no. 1, Aug. 1987, pp. 85-99. https://doi.org/10.1016/0008-6215(87)80046-0.