L-Proline, glycyl- supplier

Name
GLYCYL-L-PROLINE
EINECS 211-880-2
CAS No. 704-15-4
Article Data22
CAS DataBase
Density 1.356 g/cm³
Solubility very faint turbidity
Melting Point 185℃
Formula C₇H₁₂N₂O₃
Boiling Point 411.3 °C at 760 mmHg
Molecular Weight 172.184
Flash Point 202.6 °C
Transport Information
Appearance WHITE POWDER
Safety 26
Risk Codes 36
Molecular Structure
Hazard Symbols Xi
Synonyms L-Proline,1-glycyl-;Proline, 1-glycyl-, L- (6CI,8CI);(S)-1-(2-Aminoacetyl)pyrrolidine-2-carboxylic acid;1-Glycylproline;7: PN:WO03052099 PAGE: 83 claimed protein;Glycyl-L-proline;N-Glycyl-L-proline;N-Glycylproline;NSC 97929;
PSA 83.63000
LogP -0.34110

Synthetic route

: 23500-10-9
(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With ammonium hydroxide

: 1160-54-9
(2S)-1-(2-[[(benzyloxy)carbonyl]amino]acetyl)tetrahydro-1H-pyrrole-2-carboxylic acid

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With methanol; palladium; acetic acid Hydrogenation;
With hydrogen; palladium on activated charcoal

: 95688-74-7
1-(bromoacetyl)-L-proline

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With ammonium hydroxide

: 1-iodoacetyl-L-proline

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With ammonium hydroxide

: 56-41-7
L-alanin

: 60189-43-7
H-Gly-Pro-pNA

A: 100-01-6
4-nitro-aniline

B: 837-83-2
gly-pro-ala

C: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With dipeptidyl peptidase IV In glycerol at 40℃;
With dipeptidyl peptidase IV In glycerol at 40℃; Rate constant; Kinetics; constant of partition;

...Expand

: 60-18-4
L-tyrosine

: 60189-43-7
H-Gly-Pro-pNA

A: 22028-91-7
Gly-Pro-Tyr

B: 100-01-6
4-nitro-aniline

C: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With dipeptidyl peptidase IV In glycerol at 40℃;
With dipeptidyl peptidase IV In glycerol at 40℃; Rate constant; Kinetics; constant of partition;

...Expand

: 837-83-2
gly-pro-ala

A: 56-41-7
L-alanin

B: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
at 37℃; for 0.166667h; 0.1 M Tris HCl buffer pH 8.0, X-prolyl dipeptidyl aminopeptidase from Lactococcus lactis subsp. cremoris nTR;
at 37℃; for 0.166667h; Rate constant; 0.1 M Tris HCl buffer pH 8.0, X-prolyl dipeptidyl aminopeptidase from Lactococcus lactis subsp. cremoris nTR; Km;

: 60189-43-7
H-Gly-Pro-pNA

A: 100-01-6
4-nitro-aniline

B: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
at 37℃; for 0.166667h; 0.1 M Tris HCl buffer pH 8.0, X-prolyl dipeptidyl aminopeptidase from Lactococcus lactis subsp. cremoris nTR;
With buffer pH=7.6; dipeptidyl peptidase IV In glycerol at 30℃; Rate constant; Kinetics;
at 37℃; for 0.166667h; Rate constant; 0.1 M Tris HCl buffer pH 8.0, X-prolyl dipeptidyl aminopeptidase from Lactococcus lactis subsp. cremoris nTR; Km, Ki, competitive inhibition by dipeptides;

: 72122-62-4
L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl-glycyl-L-prolyl-L-isoleucine

A: 51871-47-7
H-Tyr-Pro-OH

B: 7669-65-0
L-phenylalanyl-L-proline

C: 89187-15-5
Gly-Pro-Ile

D: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
at 37℃; for 7h; 0.1 M Tris HCl buffer pH 8.0, X-prolyl dipeptidyl aminopeptidase from Lactococcus lactis subsp. cremoris nTR; Yield given. Yields of byproduct given;

...Expand

: 72122-62-4
L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl-glycyl-L-prolyl-L-isoleucine

A: 51871-47-7
H-Tyr-Pro-OH

B: 7669-65-0
L-phenylalanyl-L-proline

C: 89187-15-5
Gly-Pro-Ile

D: Phe-Pro-Gly-Pro-Ile

E: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
at 37℃; Kinetics; 0.1 M Tris HCl buffer pH 8.0, X-prolyl dipeptidyl aminopeptidase from Lactococcus lactis subsp. cremoris nTR;

...Expand

: 2646-61-9
Z-Gly-Pro-Leu-Gly-Pro

A: 2646-63-1
N-[1-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-L-leucine

B: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With alkaline proteinase S; tris hydrochloride In water at 37℃; for 0.166667h; hydrolysis rate;

: (S)-1-(2-Carboxyamino-acetyl)-pyrrolidine-2-carboxylic acid

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With borax; sodium dihydrogenphosphate at 26℃; Equilibrium constant;

: 60189-43-7
H-Gly-Pro-pNA

: 56-40-6
glycine

A: 100-01-6
4-nitro-aniline

B: 704-15-4
H-Gly-Pro-OH

C: 2441-63-6
Gly-Pro-Gly

Conditions

Conditions	Yield
With dipeptidyl petidase IV In glycerol at 40℃;
With dipeptidyl peptidase IV In glycerol at 40℃; Rate constant; Kinetics; constant of partition;

...Expand

: 60189-43-7
H-Gly-Pro-pNA

: 147-85-3
L-proline

A: 13100-15-7
Gly-Pro-Pro

B: 100-01-6
4-nitro-aniline

C: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With dipeptidyl peptidase IV In glycerol at 40℃;
With dipeptidyl peptidase IV In glycerol at 40℃; Rate constant; Kinetics; constant of partition;

...Expand

: 3705-27-9
(S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

A: 704-15-4
H-Gly-Pro-OH

B L-prolyl-glycine: L-prolyl-glycine

Conditions

Conditions	Yield
With sodium hydroxide

: glycyl-prolyl-4-methoxy-β-naphthylamide

A: 2764-95-6
4-methoxy-2-naphthylamine

B: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With dipeptidyl peptidase IV at 40℃; Product distribution;

: 5-glycylprolylglycyclprolyl-9-di(3-sulfonylpropyl)aminobenza[a]phenoxazolium perchlorate

A: (5-amino-benzo[a]phenoxazin-9-ylidene)-bis-(3-sulfo-propyl)-ammonium; perchlorate

B: 3705-27-9
(S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

C: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With dipeptidyl peptidase IV; HEPES buffer at 37℃; pH=7.4; Enzyme kinetics;

...Expand

: 147-85-3
L-proline

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / caustic soda / dioxane / 24 h 2: H2 / Pd-C View Scheme
Multi-step reaction with 2 steps 1: aqueous NaOH 2: aqueous NH3 View Scheme
Multi-step reaction with 2 steps 1: aqueous NaOH 2: aqueous NH3 View Scheme

: 33256-35-8
H-Pro-Gly-OMe

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 110 °C / 0 Torr 2: aqueous NaOH View Scheme

: 56-40-6
glycine

: 147-85-3
L-proline

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With recombinant His-tagged Treponema denticola ATCC35405 L-amino acid α-ligase; water; tris hydrochloride; magnesium sulfate; ATP at 37℃; for 16h; pH=8; aq. buffer; Enzymatic reaction;

: 212651-48-4
N-(9H-fluoren-9-ylmethoxycarbonyl)glycyl-L-proline

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With piperidine In N,N-dimethyl-formamide for 0.5h;

: 7-glycyl-L-prolylamino-4-methylcoumarin

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; dipeptydyl-peptidase DPP4; sodium chloride In aq. phosphate buffer at 37℃; for 0.5h; pH=7.5; Catalytic behavior; pH-value; Enzymatic reaction;

: 41863-49-4
t-butyloxycarbonyl-glycyl-proline methyl ester

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide monohydrate; water / tetrahydrofuran / 0 °C 2: trifluoroacetic acid / dichloromethane / 0 °C / Inert atmosphere View Scheme

: 14296-92-5
(S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0℃; Inert atmosphere;

: 1-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl]-L-proline methyl ester

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium hydroxide; water / tetrahydrofuran; methanol / 20 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere 3: pyridine / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 4: hydrazine hydrate / ethanol / 3 h / 20 °C / Inert atmosphere 5: water; stenotrophomonas dipeptidyl aminopeptidase IV / aq. buffer / 0.08 h / 37 °C / pH 8 / Enzymatic reaction View Scheme

Yield

Multi-step reaction with 5 steps
1: lithium hydroxide; water / tetrahydrofuran; methanol / 20 °C
2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere
3: pyridine / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
4: hydrazine hydrate / ethanol / 3 h / 20 °C / Inert atmosphere
5: water; stenotrophomonas dipeptidyl aminopeptidase IV / aq. buffer / 0.08 h / 37 °C / pH 8 / Enzymatic reaction
View Scheme

: (S)-1-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetyl]-pyrrolidine-2-carboxylic acid

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere 2: pyridine / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 3: hydrazine hydrate / ethanol / 3 h / 20 °C / Inert atmosphere 4: water; stenotrophomonas dipeptidyl aminopeptidase IV / aq. buffer / 0.08 h / 37 °C / pH 8 / Enzymatic reaction View Scheme

: C15H13ClN2O4

: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol / 3 h / 20 °C / Inert atmosphere 3: water; stenotrophomonas dipeptidyl aminopeptidase IV / aq. buffer / 0.08 h / 37 °C / pH 8 / Enzymatic reaction View Scheme

: N-(S)-1-(2-aminoacetyl)-N-(2,4-bis((E)-3,3,3-trifluoroprop-1-en-1-yl)phenyl)pyrrolidine-2-carboxamide

A: 2,4-bis[(E)-3,3,3-trifluoroprop-1-enyl]aniline

B: 704-15-4
H-Gly-Pro-OH

Conditions

Conditions	Yield
With stenotrophomonas dipeptidyl aminopeptidase IV; water In aq. buffer at 37℃; for 0.0833333h; pH=8; Enzymatic reaction;

: 34619-03-9
tert-butyldicarbonate

: 704-15-4
H-Gly-Pro-OH

: 14296-92-5
(S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In ethanol at 20 - 60℃; for 4h;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 704-15-4
H-Gly-Pro-OH

: 212651-48-4
N-(9H-fluoren-9-ylmethoxycarbonyl)glycyl-L-proline

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane for 3h;	96%

: 60-29-7
diethyl ether

: zinc(II) hydroxide

: 704-15-4
H-Gly-Pro-OH

: Zn(2+)*2NH2CH2C(O)NC3H6CHCO2(1-)*H2O*0.1(C2H5)2O=[Zn(NH2CH2C(O)NC3H6CHCO2)2]*H2O*0.1(C2H5)2O

Conditions

Conditions	Yield
In water Zn(OH)2 was added to aq. soln. of dipeptide; stirred at 60°C for 6 h; stirred at room temp. overnight; filtered; solvent removed; dissolved in methanol/ether (1/1); solvent removed; elem. anal.;	96%

...Expand

: C45H31N9O4Zn

: 704-15-4
H-Gly-Pro-OH

: C52H41N11O6Zn

Conditions

Conditions	Yield
Stage #1: C45H31N9O4Zn With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at -5 - 35℃; Inert atmosphere; Stage #2: H-Gly-Pro-OH With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	82.6%

: 3304-59-4
N-benzyloxycarbonyl-L-proline p-nitrophenyl ester

: 704-15-4
H-Gly-Pro-OH

: 70989-57-0
Z-Pro-Gly-Pro-OH

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 24h;	81%

: zinc(II) nitrate hexahydrate

: 704-15-4
H-Gly-Pro-OH

: [Zn(Gly-Pro)2]

Conditions

Conditions	Yield
In methanol for 1h;	69%

: 24424-99-5
di-tert-butyl dicarbonate

: 704-15-4
H-Gly-Pro-OH

: 14296-92-5
(S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water	67%

: 17126-94-2
N-(N-benzyloxycarbonyl-glycyl)-thioglycine S-phenyl ester

: 704-15-4
H-Gly-Pro-OH

: 91307-69-6
H-Gly-Gly-Gly-L-Pro-OH

Conditions

Conditions	Yield
With tetrahydrofuran; methanol; sodium hydroxide Hydrieren des Reaktionsprodukts in Essigsaeure enthaltendem Methanol;

: 124-38-9
carbon dioxide

: 704-15-4
H-Gly-Pro-OH

: (S)-1-(2-Carboxyamino-acetyl)-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With borax; sodium dihydrogenphosphate at 26℃; Equilibrium constant;

: 1161-13-3
N-Cbz-L-Phe

: 704-15-4
H-Gly-Pro-OH

: (S)-1-[2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-acetyl]-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With pyridine; sodium hydroxide; 5-Nitrobenz<1,6-d>-3H-1,2-oxathiole S,S-dioxide; triethylamine 1) MeCN, 2) MeCN, H2O; Yield given. Multistep reaction;

: 1027190-58-4
(2R,3R)-Oxirane-2,3-dicarboxylic acid 2-ethyl ester 3-pentafluorophenyl ester

: 704-15-4
H-Gly-Pro-OH

: 159517-32-5
N-<<(2R,3R)-3-trans(ethoxycarbonyl)oxiran-2-yl>carbonyl>-glicyl-proline

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given;

: 704-15-4
H-Gly-Pro-OH

: 72634-87-8
C7H11N2O3

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; potassium chloride In water Rate constant; Irradiation; Flash-photolysis, pH = 7;;

: 704-15-4
H-Gly-Pro-OH

A: 56-40-6
glycine

B: 147-85-3
L-proline

Conditions

Conditions	Yield
With prolidase; (trans)-1,2-cyclopentanedicarboxylic acid; water at 20℃; K+-MES buffer (pH 6.0); Ki value; other inhibitor;

: 7647-01-0
hydrogenchloride

: 704-15-4
H-Gly-Pro-OH

A: 56-40-6
glycine

B: 147-85-3
L-proline

Conditions

Conditions	Yield
at 100℃; Rate constant; Hydrolysis;

...Expand

L-Proline, glycyl- Specification

The L-Proline, glycyl-, with CAS registry number 704-15-4, belongs to the following product categories: (1)Pyrrole; (2)Biochemistry; (3)Oligopeptides; (4)Peptide Synthesis; (5)Dipeptides; (6)Dipeptides and Tripeptides; (7)Peptides. It has the systematic name of glycyl-L-proline. This chemical should be stored at the temperature of −20°C.

Physical properties of L-Proline, glycyl-: (1)ACD/LogP: -1.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.84; (4)ACD/LogD (pH 7.4): -3.94; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 49.85 Å²; (13)Index of Refraction: 1.556; (14)Molar Refractivity: 40.86 cm³; (15)Molar Volume: 126.9 cm³; (16)Polarizability: 16.19×10^-24cm³; (17)Surface Tension: 66.2 dyne/cm; (18)Density: 1.356 g/cm³; (19)Flash Point: 202.6 °C; (20)Enthalpy of Vaporization: 72.82 kJ/mol; (21)Boiling Point: 411.3 °C at 760 mmHg; (22)Vapour Pressure: 6.44E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H]1N(C(=O)CN)CCC1
(2)InChI: InChI=1/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1
(3)InChIKey: KZNQNBZMBZJQJO-YFKPBYRVBI
(4)Std. InChI: InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1
(5)Std. InChIKey: KZNQNBZMBZJQJO-YFKPBYRVSA-N

Product Name

GLYCYL-L-PROLINE

Synthetic route

L-Proline, glycyl- Specification

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