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338-69-2

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338-69-2 Usage

Chemical Properties

White Crystalline Powder

Uses

D-Alanine is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls.

Definition

ChEBI: The D-enantiomer of alanine.

General Description

Alanine is a non essential amino acid.

Biochem/physiol Actions

D-Alanine is the non-proteinogenic form of alanine which is used in bacterial cell wall biosynthesis. D-Alanine is used to study the specificity and kinetics of alanine racemase(s) (alaR).

Purification Methods

Crystallise alanine from H2O or aqueous EtOH, i.e. crystallise it from 25% EtOH in water, or recrystallise it from 62.5% EtOH, wash it with EtOH and dry it to constant weight in vacuo over P2O5. [Gutter & Kegeles J Am Chem Soc 75 3893 1953, Walsh J Biol Chem 264 2394 1989.] 2,2'-Iminodipropionic acid is a likely impurity. [Beilstein 4 IV 2480. 2481.]

Check Digit Verification of cas no

The CAS Registry Mumber 338-69-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,3 and 8 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 338-69:
(5*3)+(4*3)+(3*8)+(2*6)+(1*9)=72
72 % 10 = 2
So 338-69-2 is a valid CAS Registry Number.
InChI:InChI=1/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1

338-69-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (A0177)  D-Alanine  >98.0%(T)

  • 338-69-2

  • 5g

  • 180.00CNY

  • Detail
  • TCI America

  • (A0177)  D-Alanine  >98.0%(T)

  • 338-69-2

  • 25g

  • 590.00CNY

  • Detail
  • Alfa Aesar

  • (A10231)  D-Alanine, 99%   

  • 338-69-2

  • 5g

  • 203.0CNY

  • Detail
  • Alfa Aesar

  • (A10231)  D-Alanine, 99%   

  • 338-69-2

  • 25g

  • 850.0CNY

  • Detail
  • Alfa Aesar

  • (A10231)  D-Alanine, 99%   

  • 338-69-2

  • 100g

  • 3341.0CNY

  • Detail
  • Sigma

  • (A7377)  D-Alanine  ≥98% (HPLC)

  • 338-69-2

  • A7377-5G

  • 393.12CNY

  • Detail
  • Sigma

  • (A7377)  D-Alanine  ≥98% (HPLC)

  • 338-69-2

  • A7377-25G

  • 1,388.79CNY

  • Detail
  • Sigma

  • (A7377)  D-Alanine  ≥98% (HPLC)

  • 338-69-2

  • A7377-100G

  • 4,644.90CNY

  • Detail
  • Vetec

  • (V900378)  D-Alanine  Vetec reagent grade, ≥98%

  • 338-69-2

  • V900378-100G

  • 343.98CNY

  • Detail
  • Vetec

  • (V900378)  D-Alanine  Vetec reagent grade, ≥98%

  • 338-69-2

  • V900378-500G

  • 1,373.58CNY

  • Detail

338-69-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name D-alanine

1.2 Other means of identification

Product number -
Other names Alanine D-form

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:338-69-2 SDS

338-69-2Synthetic route

2-aminopropanamide hydrochloride
80222-96-4

2-aminopropanamide hydrochloride

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
Escherichia coli JM109; pCl38DP In various solvent(s) at 30℃; for 0.15h;100%
(3R,6S,1'S)-3,6-dimethyl-4-N-(1'-phenethyl)-1,4-morpholin-2,5-dione
174591-36-7

(3R,6S,1'S)-3,6-dimethyl-4-N-(1'-phenethyl)-1,4-morpholin-2,5-dione

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogen iodide for 1h; Heating;100%
(R)-2-(2-Oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

(R)-2-(2-Oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.5h;99%
(R)-2-((R)-2-Oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

(R)-2-((R)-2-Oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.5h; Birch reduction;99%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With isopropylamine In aq. buffer at 37℃; for 24h; pH=7.0; Enzymatic reaction;95%
With D-glucose; Bacillus subtilis glucose dehydrogenase; Symbiobacterium thermophilum meso-Diaminopimelate dehydrogenase W121L/H227I mutant; NADP; ammonium chloride In aq. buffer at 37℃; for 24h; pH=8.5; Kinetics; Reagent/catalyst; Enzymatic reaction;49%
With ammonium hydroxide; D-amino acid oxidase In phosphate buffer for 10h; pH=6.5; Reduction; Electrochemical reaction;
Conditions
ConditionsYield
With water at 170℃; for 0.05h; Microwave irradiation;95%
(R)-(+)-2-hydrazinopropionic acid
21028-13-7

(R)-(+)-2-hydrazinopropionic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide92%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

A

L-alanin
56-41-7

L-alanin

B

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With CC10H14NOSCH2CH2CH3N(CH3)2 (5); zinc diacetate In methanol at 30℃; Product distribution; pH 4.00; other reagents;A 9%
B 91%
With 5-((3-(dimethylamino)propyl)thio)-4-(aminomethyl)-3-hydroxyl-5,6,7,8-tetraquinoline In methanol at 30℃; Product distribution; stereoselective transamination at pH=4.00, various reagents and pH;A 7 % Chromat.
B 93 % Chromat.
With ethylenediaminetetraacetic acid; D-(R)-phenylalanine at 20℃; for 24h; pH=8; Product distribution; Further Variations:; Reagents; transamination;
(3R,6R)-1,4-N,N-((S)-1-phenyleth-1-yl)-3,6-dimethylpiperazine-2,5-dione
143746-61-6

(3R,6R)-1,4-N,N-((S)-1-phenyleth-1-yl)-3,6-dimethylpiperazine-2,5-dione

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogen iodide for 1h; Heating;90%
(R)-2-tert-Butoxycarbonylamino-propionic acid 2-hydroxy-ethyl ester

(R)-2-tert-Butoxycarbonylamino-propionic acid 2-hydroxy-ethyl ester

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With trimethylsilyl iodide In chloroform for 0.0833333h;88%
(R)-N-phthaloylalanine
29588-83-8

(R)-N-phthaloylalanine

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; acetone Heating;86%
trans-cyclo(D-Ala-Val)
15136-27-3

trans-cyclo(D-Ala-Val)

A

D-Alanine
338-69-2

D-Alanine

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
With hydrogenchloride; waterA 86%
B n/a
With hydrogenchlorideA 86%
B n/a
With hydrogenchloride; water for 24h; Heating;
(3R,6S)-6-tert-butyl-5-methoxy-3,6-dimethyl-3,6-dihydro-2H-1,4-oxazin-2-one

(3R,6S)-6-tert-butyl-5-methoxy-3,6-dimethyl-3,6-dihydro-2H-1,4-oxazin-2-one

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogen bromide In water at 130℃; for 24h;85%
(R)-1-(furan-2-yl)ethanamine
132523-44-5

(R)-1-(furan-2-yl)ethanamine

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With ozone In methanol at -78℃; for 0.25h;81%

A

L-alanin
56-41-7

L-alanin

B

D-Alanine
338-69-2

D-Alanine

C

D-norvaline
2013-12-9

D-norvaline

D

L-Norvaline
6600-40-4

L-Norvaline

Conditions
ConditionsYield
With (S)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 1h; Ambient temperature;A 78.31%
B 21.69%
C 60.57%
D 39.43%
With (S)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 3h; Ambient temperature;A 76.83%
B 23.15%
C 73.8%
D 26.2%
With (R)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 1h; Ambient temperature;A 26.8%
B 73.2%
C 42.16%
D 57.84%
With (R)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 1h; Ambient temperature;A 26.8%
B 73.2%
C 42.16%
D 57.84%
(1'S,5R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-methylimidazolidin-4-one
131969-00-1

(1'S,5R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-methylimidazolidin-4-one

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogenchloride In methanol for 24h; Heating;73%
C28H29N3NiO3

C28H29N3NiO3

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
Stage #1: C28H29N3NiO3 With hydrogenchloride In methanol at 70℃;
Stage #2: In water
71%
(1R,2S,5R,8S)-1,5,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one
422570-16-9

(1R,2S,5R,8S)-1,5,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
Stage #1: (1R,2S,5R,8S)-1,5,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one With hydrogenchloride at 87℃; for 2h;
Stage #2: With methyloxirane In ethanol at 20℃; for 0.5h; Further stages.;
70%
(R,S)-2-chloropropionic acid
598-78-7

(R,S)-2-chloropropionic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
70%
N-trichloroacetyl-D-alanine
137959-78-5

N-trichloroacetyl-D-alanine

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogen cation69%
With hydrogenchloride at 120℃; for 5h;69%
1-[(cyano-methyl-methyl)-amino]-5-isopropenyl-2-methyl-cyclohexane-1,3-dicarbonitrile

1-[(cyano-methyl-methyl)-amino]-5-isopropenyl-2-methyl-cyclohexane-1,3-dicarbonitrile

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 12h;37%
rac-Ala-OH
302-72-7

rac-Ala-OH

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
mittels Hefe nach reichlichem Zusatz von Zucker;
durch Penicillium glaucum;
durch Aspergillus niger;
(S)-2-bromopropanoic acid
32644-15-8

(S)-2-bromopropanoic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With ammonia; water
With ammonia
AlaOEt
17344-99-9

AlaOEt

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
und Erhitzen des erhaltenen -d-alanin-aethylester mit konz.Salzsaeure und zerlegt das entstandene d(-)-Alaninhydrochlorid mit Bleihydroxyd;
ueber N--D-alanin-aethylester;
L-Alanine ethyl ester
3082-75-5

L-Alanine ethyl ester

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With water
(R)-2-(acetylamino)propanoic acid
19436-52-3

(R)-2-(acetylamino)propanoic acid

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogenchloride
With hydrogen bromide
di-L-alanine
1948-31-8

di-L-alanine

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
durch ein im Speichel vorkommendes Ferment.Hydrolysis;
D-N-benzoylalanine
17966-60-8

D-N-benzoylalanine

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
With hydrogenchloride
benzoyl chloride
98-88-4

benzoyl chloride

rac-Ala-OH
302-72-7

rac-Ala-OH

A

L-alanin
56-41-7

L-alanin

B

D-Alanine
338-69-2

D-Alanine

Conditions
ConditionsYield
Behandeln mit Brucin, Zerlegen das Brucinsalz in die aktiven Salze, die man mit 20prozentiger Salzsaeure bei 100grad verseift;
phthalic anhydride
85-44-9

phthalic anhydride

D-Alanine
338-69-2

D-Alanine

(R)-N-phthaloylalanine
29588-83-8

(R)-N-phthaloylalanine

Conditions
ConditionsYield
for 0.05h; microwave irradiation;100%
With triethylamine In toluene Heating;90%
With pyridine for 12h; Heating;88%
D-Alanine
338-69-2

D-Alanine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
Stage #1: D-Alanine With sodium hydroxide In water at 0℃; for 0.166667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 20℃;
100%
With sodium hydroxide In tetrahydrofuran; water at 0 - 30℃; for 4.5h;98%
With triethylamine; sodium hydroxide In tetrahydrofuran; water at 20℃; for 10.5h;92%
D-Alanine
338-69-2

D-Alanine

benzyl chloroformate
501-53-1

benzyl chloroformate

N-benzyloxycarbonyl-D-alanine
26607-51-2

N-benzyloxycarbonyl-D-alanine

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 20h;100%
With sodium hydroxide In water at 0 - 20℃;92.7%
Stage #1: D-Alanine; benzyl chloroformate With sodium hydroxide In water at 0 - 20℃;
Stage #2: With hydrogenchloride In water pH=4 - 5;
89%
D-Alanine
338-69-2

D-Alanine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

(R)-N-carbethoxy-2-aminopropanoic acid
148731-47-9

(R)-N-carbethoxy-2-aminopropanoic acid

Conditions
ConditionsYield
With sodium hydroxide at 15℃; for 1h; pH=9;100%
With sodium hydrogencarbonate In water at 20℃; for 24h;90%
With sodium hydrogencarbonate
Stage #1: D-Alanine; chloroformic acid ethyl ester With sodium hydroxide at 15℃; pH=9 - 9.5;
Stage #2: With phosphoric acid In water at 0 - 5℃; pH=1;
Stage #1: D-Alanine With sodium hydroxide In water at 15℃;
Stage #2: chloroformic acid ethyl ester In water pH=9 - 9.5;
Stage #3: With phosphoric acid In water pH=1;
D-Alanine
338-69-2

D-Alanine

f6-Fmoc-OSu
916686-39-0

f6-Fmoc-OSu

f6-Fmoc-D-alanine

f6-Fmoc-D-alanine

Conditions
ConditionsYield
With sodium carbonate In water at 0 - 20℃; for 3h;100%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 3.08333h; Inert atmosphere;96%
methanol
67-56-1

methanol

D-Alanine
338-69-2

D-Alanine

D-alanine methyl ester hydrochloride
14316-06-4

D-alanine methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 2h;99%
With thionyl chloride for 8h; Heating;97%
With thionyl chloride95%
ethanol
64-17-5

ethanol

D-Alanine
338-69-2

D-Alanine

D-alanine ethyl ester hydrochloride
6331-09-5

D-alanine ethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride99%
With thionyl chloride at 40℃; for 4h;86%
D-Alanine
338-69-2

D-Alanine

Allyl chloroformate
2937-50-0

Allyl chloroformate

(R)-2-(((allyloxy)carbonyl)amino)propanoic acid
918936-47-7

(R)-2-(((allyloxy)carbonyl)amino)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 3h;99%
D-Alanine
338-69-2

D-Alanine

4-bromo-2-fluoronitrobenzene
321-23-3

4-bromo-2-fluoronitrobenzene

N-(5-bromo-2-nitrophenyl)-D-alanine

N-(5-bromo-2-nitrophenyl)-D-alanine

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 100℃; for 10h;98.2%
With potassium carbonate In ethanol; water for 10h; Reflux;91%
With potassium carbonate In ethanol; water at 80℃; for 8h;87%
formaldehyd
50-00-0

formaldehyd

D-Alanine
338-69-2

D-Alanine

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

(R)-2-(4,5-Dimethyl-3-oxy-imidazol-1-yl)-propionic acid
122459-34-1

(R)-2-(4,5-Dimethyl-3-oxy-imidazol-1-yl)-propionic acid

Conditions
ConditionsYield
In ethanol for 3h; Heating;98%
D-Alanine
338-69-2

D-Alanine

isopropyl alcohol
67-63-0

isopropyl alcohol

(R)-1-isopropoxy-1-oxopropan-2-aminium chloride
39613-92-8

(R)-1-isopropoxy-1-oxopropan-2-aminium chloride

Conditions
ConditionsYield
Stage #1: D-Alanine; isopropyl alcohol With thionyl chloride at 85℃; for 4h; Inert atmosphere;
Stage #2: With hydrogenchloride
98%
With thionyl chloride at 85℃; for 4h; Inert atmosphere;98%
With thionyl chloride at 20 - 85℃; for 4h; Inert atmosphere;98%
D-Alanine
338-69-2

D-Alanine

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

D-dodecyl 2-amino propanoate
770709-94-9

D-dodecyl 2-amino propanoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux;97.6%
D-Alanine
338-69-2

D-Alanine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

(R)-2-(2,2,2-trifluoroacetamido)propanoic acid
7592-26-9

(R)-2-(2,2,2-trifluoroacetamido)propanoic acid

Conditions
ConditionsYield
Stage #1: D-Alanine; ethyl trifluoroacetate, With N,N,N',N'-tetramethylguanidine In methanol at 20℃; for 5h;
Stage #2: With hydrogenchloride In methanol; water
97.3%
With triethylamine In methanol at 20℃; for 24h;95%
With triethylamine In methanol for 24h;86%
With triethylamine In methanol at 20℃; for 8h; Product distribution / selectivity;86%
Stage #1: D-Alanine; ethyl trifluoroacetate, With triethylamine In methanol at 20℃; for 24h;
Stage #2: for 0.166667h; Acidic conditions;
80.8%
methanol
67-56-1

methanol

D-Alanine
338-69-2

D-Alanine

D-alanine methyl ester
7625-53-8, 10065-72-2, 21705-13-5

D-alanine methyl ester

Conditions
ConditionsYield
With thionyl chloride at 60℃; for 3h;97%
With thionyl chloride at 0 - 40℃; for 4h;86%
With thionyl chloride at 20℃; for 6h;
D-Alanine
338-69-2

D-Alanine

2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

N-(2-chloroethyloxycarbonyl)-D-Ala-OH
925893-40-9

N-(2-chloroethyloxycarbonyl)-D-Ala-OH

Conditions
ConditionsYield
Stage #1: D-Alanine; 2-Chloroethyl chloroformate With sodium hydrogencarbonate In 1,4-dioxane; water
Stage #2: With hydrogenchloride In water pH=3;
97%
D-Alanine
338-69-2

D-Alanine

(4-ethynylphenyl)sulfurimidoyl difluoride

(4-ethynylphenyl)sulfurimidoyl difluoride

(N-(4-ethynylphenyl)sulfamoyl)-L-alanine

(N-(4-ethynylphenyl)sulfamoyl)-L-alanine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In aq. phosphate buffer; water; acetonitrile at 20℃; for 20h; pH=7;97%
D-Alanine
338-69-2

D-Alanine

1-decanoic acid
334-48-5

1-decanoic acid

N-decanoyl-D-alanine
22220-05-9

N-decanoyl-D-alanine

Conditions
ConditionsYield
Stage #1: 1-decanoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: D-Alanine In dichloromethane for 12h;
96%
D-Alanine
338-69-2

D-Alanine

5-bromo-4-chloro-6-phenyl-thieno[2,3-d]pyrimidine

5-bromo-4-chloro-6-phenyl-thieno[2,3-d]pyrimidine

N-(5-bromo-6-phenyl-thieno[2,3-d]pyrimidin-4-yl)-D-alanine

N-(5-bromo-6-phenyl-thieno[2,3-d]pyrimidin-4-yl)-D-alanine

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 100℃; for 1h; Inert atmosphere; Reflux;96%
D-Alanine
338-69-2

D-Alanine

C9H8BrClN2S2

C9H8BrClN2S2

(2R)-2-[(5-bromo-6-ethyl-2-methylsulfanyl-thieno[2,3-d]pyrimidin-4-yl)amino]propanoic acid

(2R)-2-[(5-bromo-6-ethyl-2-methylsulfanyl-thieno[2,3-d]pyrimidin-4-yl)amino]propanoic acid

Conditions
ConditionsYield
With potassium carbonate In ethanol; N,N-dimethyl-formamide at 100℃; Inert atmosphere;96%
D-Alanine
338-69-2

D-Alanine

R-(+)-2-bromopropionic acid
10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With hydrogen bromide; potassium bromide; sodium nitrite at 0 - 5℃; for 1h;95%
With hydrogen bromide; potassium bromide; sodium nitrite In water at -15 - 20℃; Inert atmosphere;82%
With sulfuric acid; potassium bromide; sodium nitrite at 0 - 20℃; for 2h;41%
benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate
869772-05-4

benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate

D-Alanine
338-69-2

D-Alanine

(R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid
17445-27-1

(R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;95%
D-Alanine
338-69-2

D-Alanine

benzyl alcohol
100-51-6

benzyl alcohol

(R)-benzyl 2-aminopropanoate hydrochloride
5557-81-3, 5557-83-5, 34404-37-0

(R)-benzyl 2-aminopropanoate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃;95%
D-Alanine
338-69-2

D-Alanine

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

C30H18N2O8

C30H18N2O8

Conditions
ConditionsYield
Stage #1: D-Alanine; perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With 1H-imidazole at 120℃; for 0.5h;
Stage #2: With hydrogenchloride at 85℃;
95%
With 1H-imidazole In water at 120℃; Schlenk technique; Inert atmosphere;
D-Alanine
338-69-2

D-Alanine

N-(tert-butoxycarbonyl)-D-alanine methyl ester
91103-47-8

N-(tert-butoxycarbonyl)-D-alanine methyl ester

Conditions
ConditionsYield
94%

338-69-2Relevant articles and documents

Powerful Steroid-Based Chiral Selector for High-Throughput Enantiomeric Separation of α-Amino Acids Utilizing Ion Mobility-Mass Spectrometry

Li, Yuling,Zhou, Bowen,Wang, Keke,Zhang, Jing,Sun, Wenjian,Zhang, Li,Guo, Yinlong

, p. 13589 - 13596 (2021/10/21)

Stereospecific recognition of amino acids (AAs) plays a crucial role in chiral biomarker-based diagnosis and prognosis. Separation of AA enantiomers is a long and tedious task due to the requirement of AA derivatization prior to the chromatographic or electrophoretic steps which are also time-consuming. Here, a mass-tagged chiral selector named [d0]/[d5]-estradiol-3-benzoate-17β-chloroformate ([d0]/[d5]-17β-EBC) with high reactivity and good enantiomeric resolution in regard to AAs was developed. After a quick and easy chemical derivatization step of AAs using 17β-EBC as the single chiral selector before ion mobility-mass spectrometry analysis, good enantiomer separation was achieved for 19 chiral proteinogenic AAs in a single analytical run (~2 s). A linear calibration curve of enantiomeric excess was also established using [d0]/[d5]-17β-EBC. It was demonstrated to be capable of determining enantiomeric ratios down to 0.5% in the nanomolar range. 17β-EBC was successfully applied to investigate the absolute configuration of AAs among peptide drugs and detect trace levels of-AAs in complex biological samples. These results indicated that [d0]/[d5]-17β-EBC may contribute to entail a valuable step forward in peptide drug quality control and discovering chiral disease biomarkers.

Inherently chiral dialkyloxy-calix[4]arene acetic acids as enantiodiscriminating additives for high-performance liquid chromatography separation of d,l-amino acids

Kalchenko, Olga I.,Trybrat, Oleksandr O.,Yesypenko, Oleksandr A.,Dyakonenko, Viktoriya V.,Shishkina, Svitlana V.,Kalchenko, Vitali I.

, p. 722 - 730 (2021/08/26)

Inherently chiral dialkyloxy-calix[4]arene acetic acids with asymmetric placement of substituents on the lower rim of the macrocycle were first studied as enantiodiscriminating additives to the mobile phase MeCN/H2O/HCOOH (75/25/0.02 by volume) in the high-performance liquid chromatography (HPLC) separation of d,l-alanine and d,l-valine on the achiral stationary phase ZORBAX Original CN. The dependence of enantio-binding properties on the position of alkyl groups is demonstrated. The highest resolution (1.65) and enantioselectivity (1.80) were obtained for the 1,2-dipropyloxy-calix[4]arene acetic acid.

Mechanistic Insight into the Origin of Stereoselectivity in the Ribose-Mediated Strecker Synthesis of Alanine

Legnani, Luca,Darù, Andrea,Jones, Alexander X.,Blackmond, Donna G.

supporting information, p. 7852 - 7858 (2021/05/26)

Enantioenriched amino acids are produced in a hydrolytic kinetic resolution of racemic aminonitriles mediated by chiral pentose sugars. Experimental kinetic and spectroscopic results combined with DFT computational studies and microkinetic modeling help to identify the nature of the intermediate species and provide insight into the stereoselectivity of their hydrolysis in the prebiotically relevant ribose-alanine system. These studies support a synergistic role for sugars and amino acids in the emergence of homochirality in biological molecules.

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