Reaction of glucose with some amines

161 Pages·2016·6.65 MB·English

Iowa State University Capstones, Theses and
Retrospective Theses and Dissertations
Dissertations
1943
Reaction of glucose with some amines
Ada Eleanor Mitts
Iowa State College
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Part of theBiochemistry Commons, and thePlant Sciences Commons
Recommended Citation
Mitts, Ada Eleanor, "Reaction of glucose with some amines " (1943).Retrospective Theses and Dissertations. 13725.
https://lib.dr.iastate.edu/rtd/13725
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l1
REACTIGH OP GLUCOSE WITH SOSl AMINES
by
A. Eleanor Mitts
A Thesis Sul»aitted to the Gradiiate F&Qxiltj
for the Degree of
DOCTOR OP PHILOSOPHT
Major Subjects Plant Cheaiistry
Approved!
Signature was redacted for privacy.
In Charge of Majoi^ Work
Signature was redacted for privacy.
Head of Wjor Deparliment
Signature was redacted for privacy.
bean
Iowa State College
1943
UMI Number: DP12859
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TABLE OF COSfEK!I?S
Page
IHfKODOCflCl 1
ElVIll OF LIflRATORl 7
Ammonia Derivatives of Glucose 7
l*Aminoglucose 7
2>Aminoglucose 13
3-Aminogluoose 14
3>A]Qinoglucosd 15
Phenylhydrazine Derivatives of Glucose ..... 16
Hydroxylamine Derivatives of Glucose ...... 33
Aliphatic Amine Derivatives of Glucose ..... 34
Asiide Derivatives of Glucose 39
Arcsaatlo Amine Derivatives of Glucose 39
Amine Derivatives of 2-MethylglucGae ...... 59
IXFESIMMf AL . 62
Fhenylhydrazine Derivatives of Glueoae ..... 62
Preparation of the ^hydrazide
reported by Behrend 64
Preparation of the ^hydrazone
reported by Behrend 68
Preparation of phenylbydraaine
derivatives of glucose corresponding
to derivatives of corn syrup dextrina . • 71
Hydrolysis of phenylhydrazine
derivatives of glucose and laaltose .... 78
rn 10
- iii -
Pag©
Aliphatic Amine Derivatives of Glucose 79
Preparation of glucoaylalkylamines . . . . • 79
Catalytic reduction of glucosylalkylamines « 90
Potenticaaetric titration of the
H-alkyl-d-glucaaines 98
Hydrolysis of glueosylalkylaminea 98
Attempted AsMtdori rearrangement of the
gluooaylalkylamines 106
Jjmonia Derivatives of Glucose 107
Preparation of l-arainoglucose 107
Hydrolysis of l-aminoglacose 108
Preparation of 2-aminoglucose *«....«• 112
Attempted preparation of the
p-toluidide and the K-tolyl-d-3^o-
'glucosu€ tiine fr(^ E-aminoglucose .•••.• 113
Aaide Derivatives of Glucose 114
Preparation of the 1-acyl derivatives
of loaminoglucose 114
Hydrolysis of H-acetyl-l-aminoglucose . .. . 115
Attempted condensaticm of acetamlde
with gluoose and acetobromoglucose . . « • 117
MTGrntle Amine Derivatives of Glucose ...... 119
Preparation of aryl-H-glucosides and
H-aryl-d-isoglucosaaiine 119
Hydrolysis of the H-glucosides •••*•.. 121
.teine iHsrivatives of 2-Methyiglucose 126
Phenylhydrazine derivative 126
Phenylosazcaie 127
Iv «
Page
p-5?oluidide of 2-Biethylglucose ••••«»• 128
Attempted rearrangement of p-toluidlde , . • 129
DISCUSSKM OP HiSULfS AND COHCLUSIOHS ......... 152
SUMMAiy . . . . . . . . . . . . . . . . . . 145
ACESOWXEDGMEHtS ......... ...... 147
GIfED . . . . . . . . . . . . . . . . . . . 1 4 8
1
IHfRODUCflON
Although a considerablo amount of work h&a been dotne on
the nitrogen derivatives of sugars, the literature regarding
a great many of these derivatives is very confused# The
reason for this confixsion is quit© evident when It is realized
that eaeh of these derivatives laay exists theoretically at
least, in a number of isomeric structures.
$he following diagram shows the possible structtares for
the compounds formed by the reaction of an amine, Rl]^, with
glucose:
(a) Addition
H fi
R ' .R
V,
H-C-OH HOC-H-H
BCOB HCOM
HOCE HOCH
HCOH HCOH
HCOH HCOH
HCOH KJOH
H 1
oc « and ^-Addition Compoimds of
Aldehyd o~S trueture
- 2 -
(b) Water Bllialnatlon
H 1
I \ E R
c«sa EH-C-H
I I
moM EC 01 HCOH HCOfi
I I I
IOCS BOGH HOCH 0 HOCH
I I I I
H0OH HCOl HGOH HCOH
I I I I
HOOH ISOH HG — HC^—
I I I I
mon HGOl HCOH HCOH
I I I I
H E H B
Syn and Antl Imlso ~ and ^-Pyranoside
Structure Struetur®
R
H I B
\
I
h-c-h-h
l\
HCOH HCOH
1
HOCH 0 HOCH
I
ni-J BC-
I
HCOH HCOH
i 1
HCOH HCOH
I I
H H
- and £-Furanoside
Structure