CAS 1145-80-8

N-(Benzyloxycarbonyl)-L-serine

Description:

N-(Benzyloxycarbonyl)-L-serine, also known as Z-L-serine, is a derivative of the amino acid L-serine, characterized by the presence of a benzyloxycarbonyl (Z) protecting group on the amino group. This compound is typically a white to off-white crystalline solid and is soluble in polar organic solvents such as methanol and dimethyl sulfoxide, but less soluble in non-polar solvents. It is commonly used in peptide synthesis as a protecting group for the amino group, allowing for selective reactions at the carboxyl group or side chains. The Z group can be removed under mild acidic conditions, facilitating the deprotection of the amino group when needed. N-(Benzyloxycarbonyl)-L-serine is also of interest in biochemical research and pharmaceutical applications due to its role in the synthesis of peptides and proteins. Its molecular structure includes a chiral center, making it optically active, and it exhibits properties typical of amino acids, such as the ability to participate in hydrogen bonding and form zwitterionic species in solution.

Formula: C₁₁H₁₃NO₅

InChI: InChI=1S/C11H13NO5/c13-6-9(10(14)15)12-11(16)17-7-8-4-2-1-3-5-8/h1-5,9,13H,6-7H2,(H,12,16)(H,14,15)/t9-/m0/s1

InChI key: InChIKey=GNIDSOFZAKMQAO-VIFPVBQESA-N

SMILES: C(OC(N[C@H](C(O)=O)CO)=O)C1=CC=CC=C1

Synonyms:

• (2S)-2-[(Benzyloxycarbonyl)amino]-3-hydroxypropanoic acid
• (2S)-2-[[(Benzyloxy)carbonyl]amino]-3-hydroxypropanoic acid
• (2S)-3-Hydroxy-2-(phenylmethoxycarbonylamino)propanoic acid
• (S)-2-(Benzyloxycarbonylamino)-3-hydroxypropanoic acid
• <span class="text-smallcaps">L</span>-Carbobenzyloxy serine
• <span class="text-smallcaps">L</span>-Serine, N-[(phenylmethoxy)carbonyl]-
• <span class="text-smallcaps">L</span>-Serine, N-carboxy-, N-benzyl ester
• Benzyloxycarbonyl-<span class="text-smallcaps">L</span>-serine
• Cbz-L-serine
• N-(Benzyloxycarbonyl)-<span class="text-smallcaps">L</span>-serine
• N-Benzyloxycarbonyl-L-serine
• N-Carbobenzoxy-<span class="text-smallcaps">L</span>-serine
• N-Carbobenzyloxy-<span class="text-smallcaps">L</span>-serine
• N-[(Phenylmethoxy)carbonyl]-<span class="text-smallcaps">L</span>-serine
• N-[(Phenylmethoxy)carbonyl]serine
• N-[(benzyloxy)carbonyl]-L-serine
• N-[(benzyloxy)carbonyl]serine
• N-cbz-l-serine
• NSC 286604
• Serine, N-carboxy-, N-benzyl ester, <span class="text-smallcaps">L</span>-
• Z-Ser-OH
• L-Serine, N-[(phenylmethoxy)carbonyl]-
• L-Serine, N-carboxy-, N-benzyl ester
• N-[(Phenylmethoxy)carbonyl]-L-serine

N-Benzyloxycarbonyl-L-serine

CAS: 1145-80-8

Formula: C₁₁H₁₃NO₅

Purity: >98.0%(T)(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 239.23

Ref: 3B-C0635

N-Benzyloxycarbonyl-L-serine, 99%

CAS: 1145-80-8

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: C₁₁H₁₃NO₅

Purity: 99%

Color and Shape: Powder, White

Molecular weight: 239.23

Ref: 02-A19050

Z-Ser-OH

CAS: 1145-80-8

Educt in Hoveyda’s synthesis of L-3-fluoroalanine and N-methyl-L-3-fluoroalanine derivatives via the oxazolidinone.

Formula: C₁₁H₁₃NO₅

Purity: > 99%

Color and Shape: White

Molecular weight: 239.23

Ref: 01-4001465

L-Serine, N-[(phenylmethoxy)carbonyl]-

CAS: 1145-80-8

Formula: C₁₁H₁₃NO₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 239.2246

Ref: IN-DA000EKT

Z-Ser-OH

CAS: 1145-80-8

Formula: C₁₁H₁₃NO₅

Molecular weight: 239.23

Ref: 7W-GM2492

Carbobenzyloxy-l-serine

CAS: 1145-80-8

Carbobenzyloxy-l-serine

Purity: 98%

Molecular weight: 239.22g/mol

Ref: 54-OR322046

Z-L-Serine extrapure, 99%

CAS: 1145-80-8

Formula: C₁₁H₁₃NO₅

Purity: min. 99%

Color and Shape: White to Cream powder, Crystalline powder

Molecular weight: 239.2

Ref: SR-75675

Z-Ser-OH

CAS: 1145-80-8

M03053 - Z-Ser-OH

Formula: C₁₁H₁₃NO₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 239.227

Ref: 10-M03053

N-Carboxybenzyl-L-serine-13C3

Controlled Product

CAS: 1145-80-8

Applications is an intermediate used in the synthesis of L-3-Phosphoglyceric Acid 13C3 (P358007), which is carbon-13 labelled L-3-Phosphoglyceric Acid. 3-Phosphoglyceric acid is involved in glutamate biosynthesis in syntrophus aciditrophicus. 3-Phosphoglyceric acid can also be used to study pyruvate carboxylation in SDH-deficient kidney mouse cells.
References Kim, M., et al.: Appl. Environ. Microbiol. 81, 8434 (2015); Cardaci, S., et al.: Nat. Cell. Biol. 17, 1317 (2015)

Formula: C₃C₈H₁₃NO₅

Color and Shape: Neat

Molecular weight: 242.20258

Ref: TR-C182416

N-Carboxybenzyl-L-serine

Controlled Product

CAS: 1145-80-8

Applications Building block in peptide synthesis.
References Pansare, S. V.; Org. Synth. 70, 10(1992)

Formula: C₁₁H₁₃NO₅

Color and Shape: Neat

Molecular weight: 239.22

Ref: TR-C182415

N-Cbz-L-serine

CAS: 1145-80-8

N-Cbz-L-serine is a synthetic amino acid that has been shown to have antimicrobial effects. It has been found to inhibit the growth of bacteria, fungi, and protozoa by inhibiting their cell membranes. This amino acid also inhibits the synthesis of phospholipids in bacterial cell walls and may be used as an antimicrobial agent for industrial applications. N-Cbz-L-serine contains both a hydroxy group and a hydroxyl group, which are essential for its antibacterial activity. The fatty acids present in this compound can be either saturated or unsaturated. Multigram quantities of N-Cbz-L-serine have been produced with high purity using asymmetric synthesis methods.

Formula: C₁₁H₁₃NO₅

Purity: Min. 95%

Color and Shape: White/Off-White Solid

Molecular weight: 239.22 g/mol

Ref: 3D-FC19786