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556-50-3 Usage

Description

Glycylglycine, a dipeptide formed from glycine residues, is a white crystalline compound that is the simplest of all dipeptides. It serves as a starting template for the preparation of more complex peptides and is valuable in biochemical research.

Uses

Used in Biochemical Research:
Glycylglycine is used as a buffering reagent and a starting template for the preparation of more complex peptides. It is particularly valuable for experiments investigating peptide transport and absorption.
Used in Pharmaceutical Industry:
Glycylglycine is used as a practical buffer with a buffering range of 7.5 8.9 (at 25°C), making it a valuable agent for maintaining stable pH levels in various pharmaceutical applications and experiments.
Used in Peptide Synthesis:
As the simplest dipeptide, glycylglycine serves as a fundamental building block for the synthesis of more complex peptide structures, which are essential in the development of new drugs and therapies.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 5323, 1953 DOI: 10.1021/ja01117a053

Biochem/physiol Actions

Glycine is a non-essential amino acid. Influx of calcium through the cell membrane is mediated by glycine-gated channel. Glycine participates in the synthesis of porphyrins, purine and serine. It also serves as a competitive agonist for glutamate in binding to the NMDA (N-methyl-D-aspartate) receptors. Glycine synthesis might be increased in rapidly proliferating cancer cells, due to increased demand for the amino acid. Diglycine is known to catalyze the formation of homo- and hetero dipeptides more efficiently than glycine.

Purification Methods

Crystallise glycylglycine from aqueous 50% EtOH or water at 50-60o by addition of EtOH. Dry it at 110o. It sublimes at 190-200o/0.3mm with 30% recovery [Gross & Gradsky J Am Chem Soc 77 1678 1955, King J Am Chem Soc 79 6153 1957]. [Beilstein 4 IV 2459.]

Check Digit Verification of cas no

The CAS Registry Mumber 556-50-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 6 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 556-50:
(5*5)+(4*5)+(3*6)+(2*5)+(1*0)=73
73 % 10 = 3
So 556-50-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9)

556-50-3 Well-known Company Product Price

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

  • (G0124)  Glycylglycine  >99.0%(T)

  • 556-50-3

  • 25g

  • 255.00CNY

  • Detail
  • TCI America

  • (G0124)  Glycylglycine  >99.0%(T)

  • 556-50-3

  • 100g

  • 690.00CNY

  • Detail
  • TCI America

  • (G0124)  Glycylglycine  >99.0%(T)

  • 556-50-3

  • 500g

  • 2,690.00CNY

  • Detail
  • Alfa Aesar

  • (A10523)  Glycylglycine, 99%   

  • 556-50-3

  • 25g

  • 427.0CNY

  • Detail
  • Alfa Aesar

  • (A10523)  Glycylglycine, 99%   

  • 556-50-3

  • 100g

  • 1195.0CNY

  • Detail
  • Alfa Aesar

  • (A10523)  Glycylglycine, 99%   

  • 556-50-3

  • 500g

  • 4460.0CNY

  • Detail

556-50-3Synthetic route

glycine
56-40-6

glycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With silica gel In toluene for 20h; Heating;92.4%
With zeolite Na-BETA In water at 120℃; var. silicates and pH;
Multistep reaction;
With Sodium trimetaphosphate In aq. buffer at 37℃; under 225023 Torr; pH=10.7; Pressure; Temperature;
Boc-Gly-Gly-OH
31972-52-8

Boc-Gly-Gly-OH

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane Large scale;84.9%
With trifluoroacetic acid In dichloromethane at -5℃;
Gly-Gly-MCA
208645-74-3

Gly-Gly-MCA

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; dipeptydyl-peptidase DPP5; sodium phosphate; sodium chloride In water at 37℃; for 0.5h; pH=7.0; Catalytic behavior; Enzymatic reaction;
tetrabutylphosphonium glycinate

tetrabutylphosphonium glycinate

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
Stage #1: tetrabutylphosphonium glycinate; glycine ethyl ester hydrochloride at 60℃; for 3h; Inert atmosphere;
Stage #2: With acetic acid In chloroform at 20℃; for 3h;
54%
glycylglycine ethyl ester
627-74-7

glycylglycine ethyl ester

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With 15K(1+)*H(1+)*25H2O*O122P4W34Zr(16-); water; hydrogen chloride In water-d2 at 60℃; pH=5;
glycylglycinamide
20238-94-2

glycylglycinamide

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With 15K(1+)*H(1+)*25H2O*O122P4W34Zr(16-); water; hydrogen chloride In water-d2 at 60℃; pH=5;
CbzGlyGly
2566-19-0

CbzGlyGly

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With trifluoroacetic acid
With nitromethane; hydrogen bromide
With phosphonium iodide; acetic acid at 45 - 50℃; im Wasserstoff-Strom;
N-tritylglycylglycine
5893-07-2

N-tritylglycylglycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With acetic acid
With ethanol; palladium Hydrogenation;
N--glycine

N--glycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With ethanol; hydrazine hydrate
N-carbamoyl-L-alanine
18409-49-9

N-carbamoyl-L-alanine

glycine
56-40-6

glycine

A

L-alanin
56-41-7

L-alanin

B

alanylglycine
687-69-4

alanylglycine

C

glycylglycine
556-50-3

glycylglycine

D

N-carbamoylglycine
462-60-2

N-carbamoylglycine

Conditions
ConditionsYield
In phosphate buffer at 80℃; for 1272h; pH=6.8;
glycine-glycine-glycine
556-33-2

glycine-glycine-glycine

A

glycylglycine
556-50-3

glycylglycine

B

glycine
56-40-6

glycine

Conditions
ConditionsYield
With (Et2NH2)8[{α-PW11O39Zr-(μ-OH)(H2O)}2]*7H2O; water; 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt In water-d2 at 50℃; for 24h; Reagent/catalyst;
glycyl-glycyl-L-histidine
7451-76-5

glycyl-glycyl-L-histidine

A

glycylglycine
556-50-3

glycylglycine

B

L-histidine
71-00-1

L-histidine

Conditions
ConditionsYield
With (Et2NH2)8[{α-PW11O39Zr-(μ-OH)(H2O)}2]*7H2O; water; 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt In water-d2 at 60℃; Reagent/catalyst;
chloroacetyldiglycine
15474-96-1

chloroacetyldiglycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With lithium hydroxide; water; 1,2-diamino-benzene
N-(N-benzyloxycarbonyl-glycyl)-glycine-(4-nitro-benzyl ester)
3916-37-8

N-(N-benzyloxycarbonyl-glycyl)-glycine-(4-nitro-benzyl ester)

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With hydrogenchloride; methanol; palladium on activated charcoal Hydrogenation.R 4:THF;
N-{N-[(2-nitro-phenoxy)-acetyl]-glycyl}-glycine
39522-14-0

N-{N-[(2-nitro-phenoxy)-acetyl]-glycyl}-glycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With sodium hydrogencarbonate; platinum Hydrogenation.Erhitzen des Reaktionsprodukts mit H2O;
[2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-acetylamino]-acetic acid
78641-72-2

[2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-acetylamino]-acetic acid

A

glycylglycine
556-50-3

glycylglycine

B

3,5-Dinitro-1-propyl-1H-pyridin-4-one
78641-61-9

3,5-Dinitro-1-propyl-1H-pyridin-4-one

Conditions
ConditionsYield
With propylamineA 80%
B n/a
Glycine anhydride
106-57-0

Glycine anhydride

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With lithium hydroxide
With ammonia; water
With lithium hydroxide
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Ac-Ala-DAPA-Gly-Gly-OH
121574-49-0

Ac-Ala-DAPA-Gly-Gly-OH

A

glycylglycine
556-50-3

glycylglycine

B

(S)-2-Acetylamino-N-((S)-6-oxo-2-phenylamino-5,6-dihydro-4H-[1,3]thiazin-5-yl)-propionamide

(S)-2-Acetylamino-N-((S)-6-oxo-2-phenylamino-5,6-dihydro-4H-[1,3]thiazin-5-yl)-propionamide

Conditions
ConditionsYield
With N-ethylmorpholine;; acetic acid In ethanol at 37℃; for 2.5h; Product distribution; other reagents, other times, other temp.;
H2N-GGSEFG-COOH
1419234-19-7

H2N-GGSEFG-COOH

H2N-Y-ALPETGG-COOH

H2N-Y-ALPETGG-COOH

A

glycylglycine
556-50-3

glycylglycine

B

H2N-YALPETGGSEFG-COOH
1419234-20-0

H2N-YALPETGGSEFG-COOH

Conditions
ConditionsYield
With sortase A; sodium chloride; calcium chloride In aq. buffer at 37℃; pH=7.5; Enzymatic reaction;
glycine
56-40-6

glycine

A

Glycine anhydride
106-57-0

Glycine anhydride

B

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With silica gel In toluene for 20h; Heating;A 44.3%
B 10.7%
With silica gel In toluene for 20h; Product distribution; Heating; glycine adsorbed on silica gel;
In water at 200℃; under 187515 Torr; pH=6.1; Kinetics; Equilibrium constant; Further Variations:; Temperatures;
With 2Zn(2+)*2H2O*C8MoN8(4-) at 120℃; for 840h; Reagent/catalyst; Temperature;A 20.3 %Chromat.
B 19.23 %Chromat.
glycine
56-40-6

glycine

A

sarcosine
107-97-1

sarcosine

B

N-methylglycine methylester
5473-12-1

N-methylglycine methylester

C

glycylglycine
556-50-3

glycylglycine

D

iminodiacetic acid
142-73-4

iminodiacetic acid

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen at 180℃; under 300.03 Torr; for 0.166667h;
N-chloroglycylglycine
53090-33-8

N-chloroglycylglycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With sulfite(2-) In various solvent(s) at 25℃; pH=8.59; Kinetics; Dehalogenation; UV-irradiation;
N-(N-carboxy-glycyl)-glycine
27440-15-9

N-(N-carboxy-glycyl)-glycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With borax; sodium dihydrogenphosphate at 26℃; Equilibrium constant;
2-<1-(2,5-dimethylpyrrolyl)>acetylglycine

2-<1-(2,5-dimethylpyrrolyl)>acetylglycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With potassium hydroxide; hydroxylamine hydrochloride In methanol; water for 24h; Heating; Yield given;
glycine
56-40-6

glycine

A

Glycine anhydride
106-57-0

Glycine anhydride

B

glycine-glycine-glycine
556-33-2

glycine-glycine-glycine

C

tetraglycine
637-84-3

tetraglycine

D

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With hydrogen In water at 200℃; under 187515 Torr; for 0.0333333h; Product distribution; Further Variations:; Temperatures; Reagents;
(CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH2COO))

(CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH2COO))

A

(R(c),R,S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene

(R(c),R,S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene

B

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With hydrogenchloride; sodium carbonate In water acid hydrolysis by addn. of 3N HCl, then neutralized by Na2CO3, extd. with CCl4;
(CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH2COO))

(CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH2COO))

(R,S(c),R,S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene

(R,S(c),R,S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene

B

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With hydrogenchloride; sodium carbonate In water acid hydrolysis by addn. of 3N HCl, then neutralized by Na2CO3, extd. with CCl4;
N-(chloroacetyl)glycine
6319-96-6

N-(chloroacetyl)glycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With ammonia; water
Cbz-Gly-Gly-OBn
19525-53-2

Cbz-Gly-Gly-OBn

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
N-(N-benzylsulfanylcarbonyl-glycyl)-glycine
100135-84-0

N-(N-benzylsulfanylcarbonyl-glycyl)-glycine

glycylglycine
556-50-3

glycylglycine

Conditions
ConditionsYield
With 1,4-dioxane; Perbenzoic acid; water
With Perbenzoic acid; water; benzene
With Perbenzoic acid; water; acetic acid
glycylglycine
556-50-3

glycylglycine

Glycine anhydride
106-57-0

Glycine anhydride

Conditions
ConditionsYield
With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h; Solvent; Reagent/catalyst;100%
With silica gel In gas at 180 - 200℃; under 0.08 Torr;46%
With hydrogenchloride at 150 - 160℃; im Rohr;
glycylglycine
556-50-3

glycylglycine

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

N,O-bis(trimethylsilyl)glycyl-glycine
39553-15-6

N,O-bis(trimethylsilyl)glycyl-glycine

Conditions
ConditionsYield
In acetonitrile for 2h;100%
glycylglycine
556-50-3

glycylglycine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

allyl alcohol
107-18-6

allyl alcohol

PTSA*H-Gly-Gly-OAll
1188307-54-1

PTSA*H-Gly-Gly-OAll

Conditions
ConditionsYield
In toluene Reflux; Inert atmosphere;100%
glycylglycine
556-50-3

glycylglycine

(S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate
769922-77-2

(S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate

(5S)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid
37700-64-4

(5S)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃;98%
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

glycylglycine
556-50-3

glycylglycine

Dichlorobis(diglycinato)palladium(II)
89954-58-5

Dichlorobis(diglycinato)palladium(II)

Conditions
ConditionsYield
In water stirring for etwa 13h; filtration, washing twofold with water, drying in vac., elem.anal.;98%
glycylglycine
556-50-3

glycylglycine

N,3-diphenyl-N-((trifluoromethyl)sulfonyl)propiolamide

N,3-diphenyl-N-((trifluoromethyl)sulfonyl)propiolamide

A

phenyl trifluoromethanesulfonamide
456-64-4

phenyl trifluoromethanesulfonamide

B

(3-phenylpropioloyl)glycylglycine

(3-phenylpropioloyl)glycylglycine

Conditions
ConditionsYield
In methanol; water at 20℃; for 5h; Green chemistry; chemoselective reaction;A n/a
B 97%
glycylglycine
556-50-3

glycylglycine

C52H39N5O7

C52H39N5O7

C52H42N6O7

C52H42N6O7

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 40℃;93%
indole
120-72-9

indole

formaldehyd
50-00-0

formaldehyd

glycylglycine
556-50-3

glycylglycine

N,N-bis[(1H-indol-3-yl)methyl]glycylglycine

N,N-bis[(1H-indol-3-yl)methyl]glycylglycine

Conditions
ConditionsYield
Stage #1: formaldehyd; glycylglycine In water at 55℃; Mannich Aminomethylation;
Stage #2: indole In ethanol; water at 55℃; for 0.5h; Mannich Aminomethylation;
93%
glycylglycine
556-50-3

glycylglycine

benzoyl chloride
98-88-4

benzoyl chloride

N-(N'-benzoyl-2-aminoethanoyl)-2-aminoethanoic acid
1145-32-0

N-(N'-benzoyl-2-aminoethanoyl)-2-aminoethanoic acid

Conditions
ConditionsYield
With dodecyltrimethylammonium bromide; sodium carbonate In tetrahydrofuran Heating;92%
dibutyl hydrogen phosphite
1809-19-4

dibutyl hydrogen phosphite

glycylglycine
556-50-3

glycylglycine

N-(O,O-dibutylphosphoryl)-glycyl-glycine
136884-29-2

N-(O,O-dibutylphosphoryl)-glycyl-glycine

Conditions
ConditionsYield
With triethylamine In tetrachloromethane; ethanol; water 1) -3 - 0 deg C, 7-8 h, 2) r.t., 5-6 h;92%
glycylglycine
556-50-3

glycylglycine

N2-tetrabromophthaloyl-L-aspartic anhydride
138202-17-2

N2-tetrabromophthaloyl-L-aspartic anhydride

{2-[(S)-2,5-Dioxo-3-(4,5,6,7-tetrabromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidin-1-yl]-acetylamino}-acetic acid
138202-30-9

{2-[(S)-2,5-Dioxo-3-(4,5,6,7-tetrabromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidin-1-yl]-acetylamino}-acetic acid

Conditions
ConditionsYield
In acetic acid 1.) 20 deg C, 30 min, 2.) 120 deg C;92%
glycylglycine
556-50-3

glycylglycine

[2-Oxo-2-(2-thioxo-thiazolidin-3-yl)-ethyl]-carbamic acid benzyl ester
80681-01-2

[2-Oxo-2-(2-thioxo-thiazolidin-3-yl)-ethyl]-carbamic acid benzyl ester

[2-(2-Benzyloxycarbonylamino-acetylamino)-acetylamino]-acetic acid
2566-20-3

[2-(2-Benzyloxycarbonylamino-acetylamino)-acetylamino]-acetic acid

Conditions
ConditionsYield
Ambient temperature;90%
glycylglycine
556-50-3

glycylglycine

N-succinimidyl 3-[3,3-dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b][1,4]oxazine)]-1-yl]-propionate
256235-92-4

N-succinimidyl 3-[3,3-dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b][1,4]oxazine)]-1-yl]-propionate

3-[3,3-dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b][1,4]oxazine)]-1-yl]propionylglycylglycine
256235-93-5

3-[3,3-dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b][1,4]oxazine)]-1-yl]propionylglycylglycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 6h;90%
glycylglycine
556-50-3

glycylglycine

7-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-ethyl-[1,3]dioxolo[4,5-g]quinolin-8(5H)-one
1131147-59-5

7-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-ethyl-[1,3]dioxolo[4,5-g]quinolin-8(5H)-one

2-[2-(5-ethyl-8-oxo-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxamido)acetamido]-3-acetic acid
1131147-69-7

2-[2-(5-ethyl-8-oxo-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxamido)acetamido]-3-acetic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 3h;90%
glycylglycine
556-50-3

glycylglycine

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole
1131148-55-4

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole

2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid
35665-38-4

2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;90%
glycylglycine
556-50-3

glycylglycine

allyl 1H-benzo[d][1,2,3]triazole-1-carboxylate
114416-17-0

allyl 1H-benzo[d][1,2,3]triazole-1-carboxylate

2-[2-{({allyloxy}carbonyl)amino}acetamido]acetic acid
343260-53-7

2-[2-{({allyloxy}carbonyl)amino}acetamido]acetic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;90%
glycylglycine
556-50-3

glycylglycine

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid
35665-38-4

2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 12h;89%
With sodium carbonate In 1,4-dioxane; water at 20℃;77%
glycylglycine
556-50-3

glycylglycine

copper diacetate
142-71-2

copper diacetate

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

potassium hydroxide

potassium hydroxide

K[Cu(N-2-hydroxyacetophenoneglycylglycine-3H)]*2.5H2O

K[Cu(N-2-hydroxyacetophenoneglycylglycine-3H)]*2.5H2O

Conditions
ConditionsYield
In ethanol; water N compd. dissolved in aq. EtOH (1:2) containing KOH, cooled to room temp., soln. of aromatic compd. in abs. EtOH added slowly with stirring for 1.5 h, aq. soln. of Cu compd. added dropwise, pH adjusted with KOH to 9-10, stirred at 50°C for 8 h; filtered, concd., pptd. with acetone, recrystd. from water/acetone, dried in vac. over P2O5 at 35°C; elem. anal.;89%
glycylglycine
556-50-3

glycylglycine

4-methyl-1,2,3-thiadiazol-5-ylcarbonylazide

4-methyl-1,2,3-thiadiazol-5-ylcarbonylazide

N-{[(4-methyl-1,2,3-thiadiazol-5-yl)carbamoyl]aminoacetyl}aminoacetic acid

N-{[(4-methyl-1,2,3-thiadiazol-5-yl)carbamoyl]aminoacetyl}aminoacetic acid

Conditions
ConditionsYield
In 1,4-dioxane for 3h; Reflux;89%
glycylglycine
556-50-3

glycylglycine

N-phthaloylglycine chloride
6780-38-7

N-phthaloylglycine chloride

N-[N-(N,N-phthaloyl-glycyl)-glycyl]-glycine
93923-88-7

N-[N-(N,N-phthaloyl-glycyl)-glycyl]-glycine

Conditions
ConditionsYield
Stage #1: glycylglycine With magnesium oxide In water at 25℃; for 4h;
Stage #2: N-phthaloylglycine chloride In 1,4-dioxane; water at 25℃; for 2h;
87%
With 1,4-dioxane; sodium acetate; acetic acid
With water; sodium hydrogencarbonate; benzene

556-50-3Relevant articles and documents

THE PALLADIUM(II)-PROMOTED HYDROLYSIS OF METHYL AND ISOPROPYL GLYCYLGLYCINATE

Hay, Robert W.,Pujari, Mahesh P.

, p. 1083 - 1086 (1984)

The palladium(II)-promoted hydrolysis of methyl glycylglycinate and isopropyl glycylglycinate has been studied at four temperatures (25, 30, 35, and 40 deg C) at I=0.1 mol dm-3 in the pH range 4-5.Under these conditions, and at a 1:1 metal to ligand ratio, the peptide esters act as tridentate ligands, donation occuring via the terminal amino-group, the deprotonated amide nitrogen, and the carbonyl group of the ester.Rate constants are reported for hydrolysis of the ester function by water and hydroxide ion, and activation parameters calculated.Base hydrolysis of the co-ordinated peptide esters is ca. 1E5 times faster than the unproto nated peptide esters.Mechanisms for the reactions are considered.

Kotake,Saito

, p. 853 (1966)

Destrade et al.

, p. 2590,2593,2598 (1974)

En Route to a Heterogeneous Catalytic Direct Peptide Bond Formation by Zr-Based Metal-Organic Framework Catalysts

Conic, Dragan,De Azambuja, Francisco,Harvey, Jeremy N.,Loosen, Alexandra,Parac-Vogt, Tatjana N.,Van Den Besselaar, Maxime

, p. 7647 - 7658 (2021/06/30)

Peptide bond formation is a challenging, environmentally and economically demanding transformation. Catalysis is key to circumvent current bottlenecks. To date, many homogeneous catalysts able to provide synthetically useful methods have been developed, while heterogeneous catalysts remain largely restricted to the studies addressing the prebiotic formation of peptides. Here, the catalytic activity of Zr6-based metal-organic frameworks (Zr-MOFs) toward peptide bond formation is investigated using dipeptide cyclization as a model reaction. Unlike previous catalysts, Zr-MOFs largely tolerate water, and reactions are carried out under ambient conditions. Notably, the catalyst is recyclable and no additives to activate the COOH group are necessary, which are common limitations of previous methods. In addition, a broad reaction scope tolerates substrates with bulky and Lewis basic groups. The reaction mechanism was assessed by detailed mechanistic and computational studies and features a Lewis acid activation of carboxylate groups by Zr centers toward amine addition in which an alkoxy ligand on adjacent Zr sites assists in lowering the barrier of key proton transfers. The proposed concepts were also used to study the formation of intermolecular peptide bond formation. While intrinsic challenges associated with the catalyst structure and water removal limit a more general intermolecular reaction scope under current conditions, the results suggest that further design of Zr-MOF catalysts could render these materials broadly useful as heterogeneous catalysts for this challenging transformation.

Synthesis of Deuterated or Tritiated Glycine and Its Methyl Ester

Shevchenko,Andreeva,Nagaev, I. Yu.,Myasoedov

, p. 266 - 267 (2019/01/03)

Abstract: Heating glycine (Gly) and methyl glycinate (GlyOCH3) supported on 5% Pd/C or 5% Pt/C in a deuterium or tritium gas atmosphere gave the isotope-labeled products. The experiments were carried out at 180°C for 10 min. The deuterium atom inclusion under these conditions averaged up to 1.8 atoms per molecule for Gly and up to 1.0 atom per molecule for GlyOCH3. The reaction with tritium gas gave labeled products with a specific radioactivity of 27–31 Ci/mmol for Gly and 18 Ci/mmol for GlyOCH3.

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