3D Mol Similar

N-Benzyloxycarbonyl-L-proline

: Iupac Name：(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid; CAS No.: 1148-11-4; Molecular Weight：249.26; Modify Date.: 2024-08-19 13:29; Introduction:
N-Benzyloxycarbonyl-L-proline, with the chemical formula C14H15NO4 and CAS registry number 1148-11-4, is a compound known for its applications in peptide synthesis. This white crystalline powder, also referred to as Z-Pro-OH, is characterized by its benzyloxycarbonyl (Z) protecting group on the proline amino acid. It is commonly used as a building block in the synthesis of peptides and peptidomimetics, providing stability and protection to the proline residue during the synthesis process. N-Benzyloxycarbonyl-L-proline is widely used in the pharmaceutical industry for the development of peptide-based drugs and research purposes. Its unique structure and properties make it an essential tool in the field of peptide chemistry.
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1. Names and Identifiers

: 1.1 Name; N-Benzyloxycarbonyl-L-proline; 1.2 Synonyms; (2S)-1-[(Benzyloxy)carbonyl]-2-pyrrolidinecarboxylate (2S)-1-[(Phenylmethoxy)carbonyl]pyrrolidine-2-carboxylic acid (2S)-1-Phenylmethoxycarbonylpyrrolidine-2-carboxylicacid (S)-1-(benzyloxycarbonyl)-pyrrolidine-2-carboxylic acid (S)-1-carbobenzoxypyrrolidine-2-carboxylic acid (S)-N-(benzyloxycarbonyl)-proline (S)-N-CBZ-pyrrolidine-2-carboxylic acid 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (2S)- 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI) 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, ion(1-), (2S)- 1,2-Pyrrolidinedicarboxylic acid, 1-benzyl ester, L- 1-[(Benzyloxy)carbonyl]-L-proline Benzyloxycarbonyl-L-proline Boc-Ile-OH.1/2H2O Carbobenzoxy-L-proline carbobenzoxyproline Carbobenzyloxy-L-proline Cbz-L-proline CBZ-L-Pro-OH EINECS 214-557-4 MFCD00003170 MFCD00020830 N-[(phenyl-methoxy)carbonyl]-L-proline N-benzyloxycarbonyl-(S)-proline N-Benzyloxycarbonyl-L-proline~Z-Pro-OH n-benzyloxycarbonylproline N-Carbobenzoxy-L-proline N-Carbobenzyloxy-L-proline N-Cbz-L-proline N-cbz-L-proline crystalline N-CBZ-L-Proline N-Carbobenzyloxy-L-proline N-Cbz-L-Pro-OH Z-L-Proline Z-Pro-OH; View all

1.3 CAS No.: 1148-11-4

1.4 CID: 101987

1.5 EINECS(EC#): 214-557-4

1.6 Molecular Formula: C13H15NO4 (isomer)

1.7 Inchi: InChI=1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m0/s1

1.8 InChIkey: JXGVXCZADZNAMJ-NSHDSACASA-N

1.9 Canonical Smiles: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)O

1.10 Isomers Smiles: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)O

2. Properties

2.1 Density: 1.1952 (rough estimate)

2.1 Melting point: 75-77 °C

2.1 Boiling point: 392.36°C (rough estimate)

2.1 Refractive index: -40 ° (C=2, EtOH)

2.1 Flash Point: 215.3 oC

2.1 Precise Quality: 249.100113

2.1 PSA: 66.84000

2.1 logP: 1.81010

2.1 Solubility: Solubility in methanol, almost transparency.

2.2 Appearance: white to light yellow crystal powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white to light yellow crystal powder

2.5 Color/Form: White to Yellow Solid

2.6 pKa: 3.99±0.20(Predicted)

2.7 Water Solubility: Appearance:white to off-white crystalline powder
Hazard Symbols:Not regulated
particular:particular

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Usage: An inhibitor of prolidase.

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: 62-36/37/38-20/21/22

4.1 Safety Statements: 22-24/25-36-26

4.1 Hazard Class: IRRITANT

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 RTECS: UY0745000

4.1 Specification

The?IUPAC name of?N-Carbobenzoxy-L-proline is 1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid . With the?CAS registry number 1148-11-4, it is also named as?1-(Benzyloxycarbonyl)proline ; Benzyloxycarbonyl-L-proline ; Benzyloxycarbonylproline ; Carbobenzoxy-L-proline ; Carbobenzoxy-S-proline?;?L-1,2-Pyrrolidinedicarboxylic acid 1-benzyl ester ; 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI) .

The?N-Carbobenzoxy-L-proline is white to light yellow crystal powder?which should be stored at the?temperature of?2-8 °C. It is harmful by inhalation, in contact with skin and if swallowed.?And it is irritating to eyes, respiratory system and skin.?Risk of impaired fertility.?So people should?not breathe dust and avoid contact with skin and eyes.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 1.17 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.35 ; (4)ACD/LogD (pH 7.4): -2.07 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 3.13 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 4 ; (12)Index of Refraction: 1.582 ; (13)Molar Refractivity: 63.55 cm³ ; (14)Molar Volume: 190.3 cm³ ; (15)Polarizability: 25.19×10^-24 cm³ ; (16)Surface Tension: 58.5 dyne/cm ; (17)Enthalpy of Vaporization: 72.53 kJ/mol ; (18)Vapour Pressure: 3.06E-08 mmHg at 25°C ; (19)Rotatable Bond Count: 4 ; (20)Exact Mass: 249.100108 ; (21)MonoIsotopic Mass: 249.100108 ; (22)Topological Polar Surface Area: 66.8 ; (23)Heavy Atom Count: 18.

People can use the following data to convert to the molecule structure.?SMILES: O=C(O)[C@@H]2N(C(=O)OCc1ccccc1)CCC2;?InChI: InChI=1/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m1/s1.

The following is the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravaginal	> 1gm/kg (1000mg/kg)	?	Journal of Pharmaceutical Sciences. Vol. 68, Pg. 696, 1979.

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4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY0745000

CHEMICAL NAME :: 1,2-Pyrrolidinedicarboxylic acid, 1-benzyl ester, L-

CAS REGISTRY NUMBER :: 1148-11-4

LAST UPDATED :: 199406

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C13-H15-N-O4

MOLECULAR WEIGHT :: 249.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravaginal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 280 mg/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 280 ug/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H318 Causes serious eye damage
Precautionary statement(s)
Prevention	P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

Raman : 4880 A,200 M,powder

Mass

7. Synthesis Route

1148-11-4Total: 32 Synthesis Route

100-51-6 830 Suppliers

1148-11-4 232 Suppliers

Literatures:
Zaragoza, Florencio; Stephensen, Henrik Tetrahedron Letters, 2000 , vol. 41, # 12 p. 2015 - 2017
Yield: ~81%

501-53-1 149 Suppliers

1148-11-4 232 Suppliers

Literatures:
Bulletin of the Chemical Society of Japan, , vol. 62, # 10 p. 3103 - 3108
Yield: null

6216-63-3 53 Suppliers

1148-11-4 232 Suppliers

Literatures:
De Luca, Lidia; Giacomelli, Giampaolo; Masala, Simonetta; Porcheddu, Andrea Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4999 - 5001
Yield: ~98%

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8. Precursor and Product

precursor:

501-53-1

16881-39-3

75819-24-8

200499-59-8

1148-11-4

147-85-3

61668-49-3

96452-48-1

13139-17-8

71461-30-8

609-36-9

5211-23-4

100-51-6

1885-14-9

108645-62-1

124980-30-9

200499-64-5

16652-71-4

200499-65-6

136963-34-3

200499-62-3

200499-61-2

6216-63-3

5269-62-5

39608-52-1

View all

product :

2578-57-6

2812-46-6

2812-47-7

21285-27-8

1148-11-4

34079-31-7

7801-38-9

7561-25-3

93188-01-3

147-85-3

7531-52-4

6464-80-8

88704-45-4

69261-54-7

88704-44-3

5211-23-4

2766-18-9

88704-48-7

86954-05-4

34381-71-0

1634-90-8

7784-82-9

2873-37-2

6216-63-3

2873-36-1

View all

9. Other Information

9.0 BRN: 88579

9.1 Chemical Properties: white to light yellow crystal powder

9.2 Usage: N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.

9.3 Uses: N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.

9.4 Preparation: Caution! All procedures must be carried out in an efficient fume cupboard, wearing latex gloves and chemical-proof safety goggles. ι-Proline (10.0 g, 8.7 mmol) was dissolved in 2 m sodium hydroxide solution (40 mL), and the solution was cooled to ice-water temperature. Z-Cl (20.5 g, 12 mmol) was added portionwise, with vigorous stirring or occasional shaking, over a period of 30 min at 0–5 °C to the solution of l-proline. The ice bath was then removed and stirring or occasional shaking was continued for 30 min while the reaction mixture warmed to room temperature. The mixture was then acidified to Congo red by the gradual addition of concentrated hydrochloric acid, and the oil was extracted into ethyl acetate. The extract was dried over magnesium sulfate, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was extracted/triturated with warm tetrachloromethane. The washings were decanted and the residue was further purified by recrystallization from ethyl acetate/petroleum ether.; View all

9.5 用途: Carbobenzoxyproline is an inhibitor of prolidase.

10. Computational chemical data

Molecular Weight: 249.26g/mol
Molecular Formula: C₁₃H₁₅NO₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 249.10010796
Monoisotopic Mass: 249.10010796
Complexity: 312
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 66.8
Heavy Atom Count: 18
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccByOAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHgAACAAADCjhmAYwCIMABgCIAiDSGAACAAAgAAAIiAGICIgKJjKAsTiMcAAkxgGYqAeY0SIOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

How to Prepare N-Benzyloxycarbonyl-L-proline? Jul 26 2023
L-proline is an important amino acid for synthesizing human proteins and is a crucial raw material for amino acid infusion. N-Benzyloxycarbonyl-L-proline, as its N-protected compound, is a key interme..

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