CAS 7432-21-5

N-benzyloxycarbonyl-L-tryptophan

Description:

N-Benzyloxycarbonyl-L-tryptophan, commonly referred to as Z-Trp, is a derivative of the amino acid tryptophan, characterized by the presence of a benzyloxycarbonyl (Z) protecting group. This compound is typically used in peptide synthesis as a protecting group for the amino group of tryptophan, facilitating the formation of peptide bonds without interference from the amino group. It is a white to off-white solid that is soluble in organic solvents such as dimethyl sulfoxide (DMSO) and methanol, but has limited solubility in water. The presence of the benzyloxycarbonyl group enhances the stability of the amino acid during chemical reactions, making it a valuable intermediate in organic synthesis and pharmaceutical applications. Additionally, N-Benzyloxycarbonyl-L-tryptophan can be hydrolyzed under specific conditions to release the free amino acid, which is essential for various biological functions, including protein synthesis and neurotransmitter production. Its CAS number, 7432-21-5, is used for identification in chemical databases and regulatory contexts.

Formula: C₁₉H₁₇N₂O₄

InChI: InChI=1/C19H18N2O4/c22-18(23)17(10-14-11-20-16-9-5-4-8-15(14)16)21-19(24)25-12-13-6-2-1-3-7-13/h1-9,11,17,20H,10,12H2,(H,21,24)(H,22,23)/p-1/t17-/m0/s1

InChI key: InChIKey=AHYFYYVVAXRMKB-KRWDZBQOSA-N

SMILES: c1ccc(cc1)COC(=N[C@@H](Cc1c[nH]c2ccccc12)C(=O)[O-])O

Synonyms:

• (2S)-2-[[(Benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propanoic acid
• (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate
• (2S)-3-(1H-Indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
• (S)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoic acid
• <span class="text-smallcaps">L</span>-(Carbobenzyloxy)tryptophan
• <span class="text-smallcaps">L</span>-Tryptophan, N-[(phenylmethoxy)carbonyl]-
• Benzyloxycarbonyl-<span class="text-smallcaps">L</span>-tryptophan
• Carbobenzoxy-<span class="text-smallcaps">L</span>-tryptophan
• Cbz-L-tryptophan
• Cbz-Trp-OH
• L-Tryptophan, N-[(phenylmethoxy)carbonyl]-
• N-(Benzyloxycarbonyl)tryptophan
• N-Benzyloxycarbonyl-<span class="text-smallcaps">L</span>-tryptophan
• N-Carbobenzoxy-<span class="text-smallcaps">L</span>-tryptophan
• N-Carbobenzyloxy-<span class="text-smallcaps">L</span>-tryptophan
• N-Cbz-<span class="text-smallcaps">L</span>-Trp-Oh
• N-Cbz-<span class="text-smallcaps">L</span>-Tryptophan
• N-Cbz-L-Tryptophan
• N-[(Benzyloxy)carbonyl]-L-tryptophan
• N-[(Phenylmethoxy)carbonyl]-<span class="text-smallcaps">L</span>-tryptophan
• N^α-Benzyloxycarbonyl-<span class="text-smallcaps">L</span>-tryptophan
• NSC 521831
• Na-Carbobenzyloxy-L-tryptophan
• Tryptophan, N-carboxy-, N-benzyl ester, <span class="text-smallcaps">L</span>-

N-Carbobenzoxy-L-tryptophan

CAS: 7432-21-5

Formula: C₁₉H₁₈N₂O₄

Purity: >98.0%(T)(HPLC)

Color and Shape: White to Light yellow to Light orange powder to crystal

Molecular weight: 338.36

Ref: 3B-C0638

N(α)-Benzyloxycarbonyl-L-tryptophan, 98+%

CAS: 7432-21-5

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Formula: C₁₉H₁₈N₂O₄

Purity: 98+%

Color and Shape: White to cream or pale yellow, Powder

Molecular weight: 338.36

Ref: 02-L07535

Z-Trp-OH

CAS: 7432-21-5

Bachem ID: 4001218.

Formula: C₁₉H₁₈N₂O₄

Purity: 99.9%

Color and Shape: Whitish

Molecular weight: 338.36

Ref: 01-4001218

N-Cbz-L-Tryptophan

CAS: 7432-21-5

Formula: C₁₉H₁₈N₂O₄

Purity: 97%

Color and Shape: Solid

Molecular weight: 338.3572

Ref: IN-DA00ICI8

Z-Trp-OH

CAS: 7432-21-5

Formula: C₁₉H₁₈N₂O₄

Molecular weight: 338.37

Ref: 7W-GM2976

N-Cbz-L-Tryptophan

CAS: 7432-21-5

N-Cbz-L-Tryptophan

Formula: C₁₉H₁₈N₂O₄

Purity: 98%

Molecular weight: 338.36

Ref: 54-OR1014327

Z-Trp-OH

CAS: 7432-21-5

M03036 - Z-Trp-OH

Formula: C₁₉H₁₈N₂O₄

Purity: 97%

Color and Shape: Solid, Powder

Molecular weight: 338.363

Ref: 10-M03036

Z-L-Tryptophan extrapure, 99%

CAS: 7432-21-5

Formula: C₁₉H₁₈N₂O₄

Purity: min. 99 %

Color and Shape: White to Cream to Pale yellow, Powder

Molecular weight: 338.4

Ref: SR-57591

Na-Cbz-L-tryptophan

Controlled Product

CAS: 7432-21-5

Applications Nα-Cbz-L-tryptophan is an N-Cbz-protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
References Conn, P., et al.: Proc. Nat. Acad. Sci., 83, 4086 (1986); Fink, G., et al.: Beh. Brain Res., 105, 53 (1999); Martin, R., et al.: Ann. Int. Med., 113, 124 (1990); McMenamy, R. & Oncley, J.: J. Biol. Chem., 233, 1436 (1958); Terness, P., et al.: J. Exp. Med., 196, 447 (2002); Widner, B., et al.: Clin. Chem., 43, 2424 (1997)

Formula: C₁₉H₁₈N₂O₄

Color and Shape: Neat

Molecular weight: 338.36

Ref: TR-C227795