Synthesis of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine analogues. n-Butyramide, 3-chloropropionamide, 3-aminopropionamide, and isovaleramide analogues

Article abstract of DOI:10.1016/S0008-6215(01)00057-X

The syntheses of four analogues of N⁴-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-β-D-glucopyranosylamine. n-Butyric anhydride gave N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N¹-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3- aminopropionamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)isovaleramide.

Full text of DOI:10.1016/S0008-6215(01)00057-X

www.elsevier.nl/locate/carres
Carbohydrate Research 331 (2001) 439–444
Note
Synthesis of
N4-(2-acetamido-2-deoxy-b-
D-glucopyranosyl)- -
L
asparagine analogues. n-Butyramide,
3-chloropropionamide, 3-aminopropionamide, and
isovaleramide analogues
Jerry J. Kaylor, John M. Risley*
Department of Chemistry, The Uni6ersity of North Carolina at Charlotte, 9201 Uni6ersity City Boule6ard,
Charlotte, NC 28223-0001, USA
Received 21 December 2000; accepted 12 February 2001
Abstract
The syntheses of four analogues of N4-(2-acetamido-2-deoxy-b-
D
-glucopyranosyl)-
L-asparagine are described.
Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-b-
gave N-(2-acetamido-2-deoxy-b- -glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized
from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-b- -glucopyranosyl)-3-chloropropionamide. Equili-
-glucopyranosyl)-3-aminopropi-
D
-glucopyranosylamine. n-Butyric anhydride
D
D
bration of the latter with ammonium bicarbonate gave N1-(2-acetamido-2-deoxy-b-
D
onamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-b-D-glucopyranosyl)-
isovaleramide. © 2001 Elsevier Science Ltd. All rights reserved.
Keywords: b-N-Acetylglucosaminyl-L-asparagine analogues; n-Butyric acid analogue; 3-Chloropropionic acid analogue; 3-
Aminopropionic acid analogue; Isovaleric acid analogue
Glycosylasparaginase ((GA), aspartylglu-
active site fingerprint of GA, we have synthe-
cosaminidase (AGA), N4-(b-N-acetyl-
D
-glu-
sized analogues of the natural substrate, N4-
cosaminyl)-
L
-asparaginase;
EC
3.5.1.26)
(2-acetamido-2-deoxy-b-
D
-glucopyranosyl)-
catalyzes the hydrolysis of the amide bond
between N-acetylglucosamine and asparagine
in the principle linkage of N-linked glyco-
proteins and is a key enzyme in the catabolism
of N-linked glycoproteins.1 For a study of the
L
-asparagine ((GlcNAc-)Asn).2–4 To further
this study, we required the GlcNAc(b1-N)-n-
butyramide 1, 3-chloropropionamide 2, 3-
aminopropionamide 3, and isovaleramide 4
analogues of the amino acid of (GlcNAc-
)Asn, which possess no free carboxyl groups.
The syntheses of these four analogues are
described in this paper. The 3-aminopropi-
onamide 3 analogue is of particular interest as
* Corresponding author. Tel.: +1-704-6874844; fax: +1-
704-6873151.
E-mail address: jmrisley@email.uncc.edu (J.M. Risley).
0008-6215/01/$ - see front matter © 2001 Elsevier Science Ltd. All rights reserved.
PII: S0008-6215(01)00057-X

440
J.J. Kaylor, J.M. Risley / Carbohydrate Research 331 (2001) 439–444
the analogue of (GlcNAc-)Asn where the a-
carboxyl group has been substituted with a
hydrogen; it may also have application for
incorporation into C-terminal glycopeptides
containing no C-terminal carboxyl group.
Compounds 6 and 7 were used without fur-
ther purification.
Repeated attempts to synthesize 1, 2, and 4
in single, large reactions of 5 with n-butyric
anhydride, 6, and 7, respectively, were not
successful (Scheme 1). While this may be un-
derstood in terms of possible miscibility prob-
lems of the n-butyric anhydride and water,
which were not encountered with anhydrides
we used in the synthesis of other analogues,2,4
it is not clear why the reactions were not
successful for 6 and 7 performed in dimethyl
sulfoxide, which has been shown to be a good
solvent for formation of the N-glycosylic
bond.7,8 It was found that a set of smaller
reactions could be prepared that were success-
ful. The reactions of n-butyric anhydride, 6,
and 7 with the b amino group of 5 occurred
exclusively at the amino group to form the
N-glycosylic bond, which followed the well-es-
tablished preference of activated carboxylic
acids to react with the amino group to form
the N-glycosylic (amide) bond rather than
with the sugar hydroxyl groups on carbohy-
drate molecules (Refs. 2–4 and references
cited therein). Thus, although 5, used in the
reaction, contained approximately 30% Glc-
NAc, the reaction of 5 with n-butyric anhy-
dride, 6, and 7, did not occur with a sugar
hydroxyl group to form a carboxylate ester
between GlcNAc and the acids. The synthesis
of 3 from 2 was based on the amination
The syntheses of the four analogues, 1, 2, 3,
and 4, of (GlcNAc-)Asn utilizing 2-acetamido-
2-deoxy-b- -glucopyranosylamine (5) required
D
activated carboxylic acids. While there are
many methods to activate a carboxylic acid,
we chose the anhydride because we have had
previous success in the synthesis of other ana-
logues.2,4 n-Butyric acid was commercially
available as n-butyric anhydride, while 3-
chloropropionic acid and isovaleric acid re-
quired activation. Attempted synthesis of
3-chloropropionic anhydride (6) using (1) 1:1
thionyl chloride–acetyl chloride5 was not suc-
cessful; (2) thionyl chloride gave very low
yields; and (3) 1:1 N-hydroxysuccinimide–
N,N%-dicyclohexylcarbodiimide6 gave low
yields; finally, using N,N%-dicyclohexylcar-
bodiimide alone, the synthesis of 6 was suc-
cessful. Attempted synthesis of isovaleric
anhydride using (1) 1:1 thionyl chloride–ace-
tyl chloride5 gave the acetic isovaleric mixed
anhydride and (2) thionyl chloride gave no
anhydride. Because activation of isovaleric
acid as the anhydride proved difficult, we
attempted to prepare the succinimidyl deriva-
tive, and succinimidyl isovalerate 7 was syn-
thesized successfully from N-hydroxysuccini-
mide and N,N%-dicyclohexylcarbodiimide.6
reaction of N-(2-acetamido-2-deoxy-b- -glu-
D
copyranosyl)chloroacetamide with ammonium
carbonate to give N1-(2-acetamido-2-deoxy-b-
D
-glucopyranosyl)glycinamide.9 When we at-
tempted to use ammonium carbonate or
ammonium chloride with 2, only the elimina-
tion, vinyl, product was obtained, as shown by
1H NMR signals at l 5.5–6.5. We found that
ammonium bicarbonate gave 3 as the hydro-
chloride salt. The four analogues, 1, 2, 3, and
4, were purified by reversed-phase HPLC. The
properties of each analogue indicated their
successful synthesis. However, the purified
yields were lower than expected based on our
previous experience. The low yield of 1 may
be understood, again, in terms of the possible
miscibility problem of the n-butyric anhydride
and water. A homogeneous solution was ob-
tained at the end of the reaction, and therefore
Scheme 1.

J.J. Kaylor, J.M. Risley / Carbohydrate Research 331 (2001) 439–444
441
propionic acid from Janssen Chemica;
n-butyric anhydride, N,N%-dicyclohexylcar-
bodiimide, and N-hydroxysuccinimide from
Sigma; NH4HCO3 from Spectrum. All other
chemicals were at least analytical grade.
the competing hydrolysis reaction of the anhy-
dride was significant. The low yields of 2 and
4 would indicate that, under the conditions of
the reactions used here, the formation of the
amide bond was very slow. To remove the
dimethyl sulfoxide solvent used in these two
reactions, the combined samples were ex-
tracted with diethyl ether; any unreacted 6 or
7 was removed at this step in the procedure,
but analysis of these extracts was not carried
out. Unreacted 5 or GlcNAc and the ana-
logues were well separated on reversed-phase
HPLC, and therefore no further analysis of
the reaction was done. As we observed, 2 is
prone to undergo elimination in the amination
reaction to 3, and therefore the low yield of 3
from 2 by amination with ammonium bicar-
bonate is a consequence of the side-elimina-
tion reaction to give the vinyl analogue, which
eluted well separated from 3 on reversed-
phase HPLC. While these procedures pro-
vided sufficient quantities of the four
analogues for our studies, an increased yield
may be possible utilizing other procedures, as
for example in Refs. 7, 8 and 10. The nomen-
clature used to assign the NMR signals fol-
lows that used for (GlcNAc-)Asn.11 The NMR
spectra agree with data reported for (GlcNAc-)-
Asn11 and other analogues.2–4 The characteris-
General methods.—A GE 300 spectrometer
1
was used to record NMR spectra. H NMR
spectra were recorded at 300.2 MHz in a
5-mm probe at ambient temperature with a
2000 Hz sweep width, 30° pulse angle, and an
8k data block; no line-broadening factor was
applied to the accumulated FID. Natural
13
abundance C NMR spectra were recorded at
75.5 MHz in a 5-mm probe at ambient tem-
perature with a 10,000 Hz sweep width, 30°
pulse angle, and an 8k data block; protons
were broad-band decoupled and a line-broad-
ening factor of 2.0 Hz was applied to the
accumulated FID. The error in the measured
1
chemical shifts is 90.002 ppm for H NMR
and 90.032 ppm for 13C NMR; the error in
the measured coupling constants is 90.50 Hz.
Reversed-phase HPLC was carried out on a
BioRad model 2800 liquid chromatograph
equipped with a BioRad UV 1806 UV–Vis
detector and a Whatman Partisil 10 ODS-3
M/9-50 preparative column. Water was used
as the mobile phase at a flow rate of 3.0 or 5.0
mL/min, and the column was monitored at
195 nm. Evaporation of solvents was con-
ducted on a rotary evaporator at ꢀ60–70 °C
at water aspirator vacuum. Elemental analyses
were done at Atlantic Microlabs, Inc. (Nor-
cross, GA).
1
tic doublet for the anomeric proton in the H
NMR spectrum appears at lꢀ5.05 with
1
J1,2ꢀ9.77 Hz.11,12 The H NMR signals for
the 1,2-disubstituted ethane groups in 2 and 3
might be expected to have AA%BB% spectra,
but they are first order, as are all of the signals
for each analogue. However, of note is the
non-equivalence of the two g-methyl groups in
Preparation of 2-acetamido-2-deoxy-i-
glucopyranosylamine2–4 (5).—2-Acetamido-2-
deoxy- -glucopyranose (GlcNAc) was
D
-
D
13
dissolved in satd aq NH4HCO3 (ꢀ1.5 M) to
give a molar ratio of 5:1 ammonia–sugar. The
reaction was allowed to proceed to equi-
librium at 40 °C with intermittent addition of
solid NH4HCO3 to maintain saturation. Fol-
lowing removal of excess NH4HCO3 by evap-
oration at 40 °C and rotary evaporation, the
white solid contained 70% 5 and 30% of the a
and b anomers of GlcNAc as determined by
4 that appear as two doublets. The C NMR
signals for each analogue could be assigned
without difficulty.
1. Experimental
Materials.—Chemicals purchased from the
following suppliers were: deuterium oxide
2
2
1
(99.9 atom% H), CHCl3-d (99.8 atom% H),
integration of the H NMR signals in D2O for
2
and acetone-d6 (99.9 atom% H) from Cam-
anomeric protons of l 4.142 (J1,2 8.79 Hz), l
5.180 (J1,2 3.42 Hz), and l 4.324 (J1,2 9.76 Hz),
respectively, and was used without further
purification.
bridge Isotopes Laboratories; isovaleric acid
from Eastman Organic Chemicals; 2-acetam-
ido-2-deoxy- -glucopyranose and 3-chloro-
D

442
J.J. Kaylor, J.M. Risley / Carbohydrate Research 331 (2001) 439–444
N-(2-Acetamido-2-deoxy-i- -glucopyran-
D
N-(2-Acetamido-2-deoxy-i- -glucopyran-
D
osyl)-3-chloropropionamide hydrate (2).—
Compound 5 (50 mg, 0.227 mmol) was dis-
solved in dimethyl sulfoxide (ten drops), and
compound 6 (47.6 mg, 0.239 mmol) was
added.2,13 A total of 18 sample vials were
prepared. The samples were vortexed at rt
overnight. The samples were combined, and
the solvent was extracted with Et2O (six
aliquots of 50 mL each). Evaporation of resid-
ual Et2O left an oily residue that was dissolved
in water and purified by HPLC in fractions.
Eluent with a retention time between 20.2 and
24.5 min (depending on fraction size) was
collected. The eluents were combined and
lyophilized to give 350 mg (28%) of 2 as a
fluffy, white crystalline solid: mp 201.3–
osyl)-n-butyramide hydrate (1).—Compound 5
(50 mg, 0.227 mmol) was dissolved in water
(four drops) and n-butyric anhydride (37.2
mL, 0.227 mmol) was added.2,13 A total of 15
sample vials were prepared. The samples were
vortexed at rt for 1 h; any solid that formed
was dissolved by addition of a minimal
amount of water. The samples were combined
and purified by HPLC in fractions. Eluent
with a retention time between 29.0 and 40.0
min (depending on fraction size) was col-
lected. The eluents were combined and
lyophilized to give 257 mg (26%) of 1 as fluffy,
1
white crystals: mp 233.5–235.0 °C; H NMR
(D2O, reference acetone (2.225 ppm)): l 0.855
(t, 3 H, Jb,g 7.33 Hz, H-g (CH3)), 1.585 (m, 2
H, Ja,b 7.33 Hz, H-b (CH2)), 1.979 (s, 3 H,
COCH3), 2.221 (t, 2 H, H-a (CH2)), 3.457 (dd,
1 H, J3,4 9.92, J4,5 8.81 Hz, H-4 (CHOH)),
3.520 (m, 1 H, J5,6a 2.46, J5,6b 3.42 Hz, H-5
(CHOꢀ)), 3.586 (dd, 1 H, J2,3 10.26 Hz, H-3
(CHOH)), 3.729 (dd, 1 H, J6a,6b −12.04 Hz,
H-6b (CH2OH)), 3.797 (dd, 1 H, J1,2 9.76 Hz,
H-2 (CHNHAc)), 3.864 (dd, 1 H, H-6a
(CH2OH)), 5.025 (d, 1 H, H-1 (CHNH)); 13C
NMR (D2O, reference p-dioxane (66.667
ppm)): l 13.552 (C-g), 19.827 (C-b), 22.964
(COCH3), 38.715 (C-a), 55.340 (C-2), 61.517
(C-6), 70.541 (C-4), 75.199 (C-3), 78.627 (C-5),
79.306 (C-1), 175.625 (COCH3), 178.827
(NHCO). Anal. Calcd for C12H22N2O6·
0.5H2O: C, 48.18; H, 7.75; N, 9.37. Found: C,
48.30; H, 7.39; N, 9.31.
1
202.0 °C; H NMR (D2O, reference acetone
(2.225 ppm)): l 1.934 (s, 3 H, COCH3), 2.680
(t, 2 H, Ja,b 7.08 Hz, H-a (CH2)), 3.424 (dd, 1
H, J3,4 9.28, J4,5 10.72 Hz, H-4 (CHOH)),
3.483 (m, 1 H, J5,6a 1.95, J5,6b 4.89 Hz, H-5
(CHOꢀ)), 3.554 (dd, 1 H, J2,3 10.74 Hz, H-3
(CHOH)), 3.694 (dd, 1 H, J6a,6b −11.74 Hz,
H-6b (CH2OH)), 3.728 (t, 2 H, H-b (CH2Cl)),
3.764 (dd, 1 H, J1,2 9.77 Hz, H-2 (CHNHAc)),
3.820 (dd, 1 H, H-6a (CH2OH)), 5.054 (d, 1
H, H-1 (CHNH)); 13C NMR (D2O, reference
p-dioxane (66.667 ppm)): l 23.158 (COCH3),
39.621 (C-a), 41.109 (C-b), 55.372 (C-2),
61.485 (C-6), 70.477 (C-4), 75.166 (C-3),
78.692 (C-5), 79.306 (C-1), 174.719 (COCH3),
175.689 (NHCO). Anal. Calcd for C11H19-
ClN2O6·0.25H2O: C, 41.91; H, 6.23; Cl, 11.25;
N, 8.89. Found: C, 41.87; H, 6.01; Cl, 10.99;
N, 8.55.
Preparation of 3-chloropropionic anhydride
(6).—Using the basic procedure of Ouihia et
al.,6 3-chloropropionic acid (2.0 g, 18.4 mmol)
was dissolved in CH2Cl2 (40 mL). N,N%-Dicy-
clohexylcarbodiimide (3.8 g, 18.4 mmol) was
added slowly with stirring. After the addition
was completed, the solution was stirred for 5
min and filtered to remove dicyclohexylurea.
The precipitate was washed with CH2Cl2 and
the filtrates were combined. Solvent was re-
moved by rotary evaporation to give a vis-
N1-(2-Acetamido-2-deoxy-i-
-glucopyran-
D
osyl)-3-aminopropionamide hydrochloride di-
hydrate (3).—Using a modification of Manger
et al.,9 compound 2 (50 mg, 0.227 mmol) was
dissolved in water (0.5 mL) in a glass ampule
containing a stir bar. NH4HCO3 (0.5 g, 6.41
mmol) was added. Two ampules were pre-
pared. Each ampule was sealed, placed in an
oil bath at 40–50 °C, and stirred for 2 days.
The ampules were broken, and the solutions
combined and filtered through glass wool.
Water (3 mL) was added to the filtrate, and
the solution was placed in a water bath at
40 °C for 2 h to evaporate residual NH4HCO3.
The product was purified by HPLC in frac-
1
cous, yellowish, opaque liquid (1.275 g). H
NMR (CDCl3) showed the sample contained
65% 6 by integration of the two methylene
groups at l 2.85 and 3.75 for the acid and l
2.95 and 3.85 for the anhydride, and was used
without further purification.

J.J. Kaylor, J.M. Risley / Carbohydrate Research 331 (2001) 439–444
443
residue with suspended white lumps that was
dissolved in water and purified by HPLC in
fractions. Eluents with a retention time be-
tween 44.4 and 54.3 min (depending on frac-
tion size) was collected. The eluents were
combined and lyophilized to give 206 mg
(20%) of 4 as a fluffy, white crystalline solid:
tions. Eluent with a retention time between 6.0
and 10.5 min (depending on fraction size) was
collected. The eluents were combined and
lyophilized to give 17 mg (18%) of 3 as very
hygroscopic, sticky, white crystals: mp 189.1–
1
191.0 °C; H NMR (D2O, reference acetone
(2.225 ppm)): l 2.006 (s, 3 H, COCH3), 2.689
(t, 2 H, Ja,b 6.59 Hz, H-a (CH2)), 3.245 (t, 2 H,
H-b (CH2)), 3.473 (dd, 1 H, J3,4 10.25, J4,5 8.30
Hz, H-4 (CHOH)), 3.540 (m, 1 H, J5,6a 2.00,
J5,6b 5.13 Hz, H-5 (CHOꢀ)), 3.613 (dd, 1 H,
J2,3 9.76 Hz, H-3 (CHOH)), 3.744 (dd, 1 H,
J6a,6b −12.45 Hz, H-6b (CH2OH)), 3.829 (dd,
1 H, J1,2 9.77 Hz, H-2 (CHNHAc)), 3.879 (dd,
1 H, H-6a (CH2OH)), 5.071 (d, 1 H, H-1
(CHNH)); 13C NMR (D2O, reference p-diox-
ane (66.667 ppm)): l 23.029 (COCH3), 33.185
(C-a), 36.387 (C-b), 55.210 (C-2), 61.517 (C-
6), 70.509 (C-4), 75.166 (C-3), 78.595 (C-5),
79.339 (C-1), 173.975 (COCH3), 175.819
(NHCO). Anal. Calcd for C11H21N3O6·
HCl·2H2O·2.5NH4Cl: C, 26.56; H, 7.29; N,
15.48. Found: C, 26.64; H, 6.56; N, 15.44.
Preparation of succinimidyl iso6alerate
(7).—Using the basic procedure of Ouihia et
al.,6 isovaleric acid (2.15 mL, 19.58 mmol) was
placed in CH2Cl2 (40 mL), and N-hydroxysuc-
cinimide (2.25 g, 19.55 mmol) was added and
dissolved. The solution was stirred at rt, and
N,N%-dicyclohexylcarbodiimide (3.8 g, 18.4
mmol) was added slowly. After 1 week dicy-
clohexylurea was removed by filtration and
washed with CH2Cl2. The filtrates were com-
bined, and the solvent was removed on a
rotary evaporator to give a viscous, cloudy,
1
mp 245.8–247.5 °C; H NMR (D2O, reference
acetone (2.225 ppm)): l 0.880 (d, 3 H, Jb,g 6.35
Hz, H-g (CH3)), 0.910 (d, 3 H, Jb,g% 6.83 Hz,
H-g% (CH3)), 1.980 (m, 1 H, Ja,b 7.32 Hz, H-b
(CH)), 1.986 (s, 3 H, COCH3), 2.133 (d, 2 H,
H-a (CH2)), 3.469 (dd, 1 H, J3,4 9.28, J4,5 8.55
Hz, H-4 (CHOH)), 3.536 (m, 1 H, J5,6a 2.35,
J5,6b 5.37 Hz, H-5 (CHOꢀ)), 3.594 (dd, 1 H,
J2,3 10.01 Hz, H-3 (CHOH)), 3.741 (dd, 1 H,
J6a,6b −12.45 Hz, H-6b (CH2OH)), 3.812 (dd,
1 H, J1,2 9.77 Hz, H-2 (CHNHAc)), 3.875 (dd,
1 H, H-6a (CH2OH)), 5.054 (d, 1 H, H-1
(CHNH)); 13C NMR (D2O, reference p-diox-
ane (66.667 ppm)): l 22.220 (C-g), 22.479
(C-g%), 23.029 (COCH3), 27.169 (C-a), 46.057
(C-b), 55.243 (C-2), 61.517 (C-6), 70.509 (C-
4), 75.263 (C-3), 78.627 (C-5), 79.209 (C-1),
175.592 (COCH3), 178.309 (NHCO). Anal.
Calcd for C13H24N2O6·0.5H2O: C, 49.86; H,
8.05; N, 8.95. Found: C, 49.59; H, 7.80; N,
8.89.
Acknowledgements
This research was supported by a Cottrell
College Science Award of Research Corpora-
tion. Acknowledgment is made to the Donors
of the Petroleum Research Fund, adminis-
tered by the American Chemical Society, for
partial support of this research. This research
was supported, in part, by funds provided by
the University of North Carolina at Charlotte.
1
white liquid (2.637 g). H NMR (acetone-d6)
showed the sample contained a minimum 90%
of 7 by integration of the isovaleric C-2 meth-
ylene group at l 2.33 for the acid and l 2.45
for the anhydride. The product was used with-
out further purification.
N-(2-Acetamido-2-deoxy-i- -glucopyran-
D
osyl)iso6aleramide hydrate (4).—Compound 5
(50 mg, 0.227 mmol) was dissolved in
dimethyl sulfoxide (ten drops), and compound
7 (47.8 mg, 0.240 mmol) was added.2,13 A total
of 15 sample vials were prepared. The samples
were vortexed at rt for 1 week. The samples
were combined, and the solvent was extracted
with Et2O (six aliquots of 50 mL each). Evap-
oration of residual Et2O left a viscous, oily
References
[1] Aronson, Jr., N. N. Biochim. Biophys. Acta 1999, 1455,
139–154.
[2] Xia, Y. -Q.; Risley, J. M. J. Carbohydr. Chem. 2001, 20,
45–55.
[3] Huang, D. H.; Risley, J. M. Carbohydr. Res. 2000, 329,
487–493.
[4] Malik, J. J.; Risley, J. M. Magn. Reson. Chem. 2001, 39,
98–100.

444
J.J. Kaylor, J.M. Risley / Carbohydrate Research 331 (2001) 439–444
[5] Naps, M.; Johns, I. B. J. Am. Chem. Soc. 1940, 62,
2450–2457.
[6] Ouihia, A.; Rene, L.; Guilhem, J.; Pascard, C.; Badet, B.
J. Org. Chem. 1993, 58, 1641–1642.
[7] Cohen-Anisfeld, S. T.; Lansbury, Jr., P. T. J. Am. Chem.
Soc. 1993, 115, 10531–10537.
[8] Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.;
Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549–560.
[9] Manger, I. D.; Rademacher, T. W.; Dwek, R. A. Bio-
chemistry 1992, 31, 10724–10732.
[10] Lubineau, A.; Auge, J.; Drouillat, B. Carbohydr. Res.
1995, 266, 211–219.
[11] Vliegenthart, J. F. G.; Dorland, L.; van Halbeek, H. Ad6.
Carbohydr. Chem. Biochem. 1983, 41, 209–373.
[12] Monsigny, M.; Que´tard, C.; Bourgerie, S.; Delay, D.;
Pichon, C.; Midoux, P.; Mayer, R.; Roche, A. C.
Biochimie 1998, 80, 99–108.
[13] Urge, L.; Jackson, D. C.; Gorbics, L.; Wroblewski, K.;
Graczyk, G.; Otvos, Jr., L. Tetrahedron 1994, 50, 2373–
2390.
.
.