118552-55-9

Basic information

• Product Name: N-BOC-DL-PIPECOLINIC ACID
• Synonyms: 1-N-BOC-2-PIPERIDINECARBOXYLIC ACID;1-(TERT-BUTOXYCARBONYL)PIPERIDINE-2-CARBOXYLIC ACID;(+/-)-1-BOC-PIPERIDINE-2-CARBOXYLIC ACID;BOC-DL-PIPECOLIC ACID;BOC-DL-PIP-OH;BOC-DL-PIC(2)-OH;BOC-DL-HOMOPROLINE;BOC-DL-HOMOPRO-OH
• CAS NO: 118552-55-9
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.27
• Product Categories: chiral;Chiral Reagent
• Mol File: 118552-55-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 353.2oC at 760 mmHg
• Flash Point: 167.41oC
• Appearance: /
• Density: 1.164g/cm3
• Vapor Pressure: 6.15E-06mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: N-BOC-DL-PIPECOLINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-DL-PIPECOLINIC ACID(118552-55-9)
• EPA Substance Registry System: N-BOC-DL-PIPECOLINIC ACID(118552-55-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 118552-55-9(Hazardous Substances Data)

Usage

General Description

N-BOC-DL-PIPECOLINIC ACID is a compound that belongs to the family of pipecolic acid derivatives, which are commonly utilized in the synthesis of pharmaceuticals and organic compounds. It is a derivative of pipecolinic acid with a BOC (tert-butyloxycarbonyl) protecting group attached to the nitrogen atom. The BOC group serves to protect the amine functionality of the pipecolinic acid, allowing for controlled reactions and increased stability. N-BOC-DL-PIPECOLINIC ACID is often used in peptide synthesis and as a building block for the preparation of various pharmaceutical agents and bioactive compounds.

InChI:InChI=1/C11H19NO4/c1-11(2,3)16-10(15)12-7-5-4-6-8(12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)/p-1/t8-/m0/s1

Downstream Products

• 552318-55-5 2-[({[(benzyloxycarbonylmethyl-carbamoyl)-methyl]-carbamoyl}-methyl)-carbamoyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 126789-44-4 C₈₀H₁₅₅NO₁₁S₂Si₄ 

Relevant articles and documents

Discovery of 23 Natural Tubulysins from Angiococcus disciformis An d48 and Cystobacter SBCb004

The tubulysins are a family of complex peptides with promising cytotoxic activity against multi-drug-resistant tumors. To date, ten tubulysins have been described from the myxobacterial strains Angiococcus disciformis An d48 and Archangium gephyra Ar 315. We report here a third producing strain, Cystobacter sp. SBCb004. Comparison of the tubulysin biosynthetic gene clusters in SBCb004 and An d48 reveals a conserved architecture, allowing the assignment of cluster boundaries. A SBCb004 strain containing a mutant in the putative cyclodeaminase gene tubZ accumulates pretubulysin A, the proposed first enzyme-free intermediate in the pathway, whose structure we confirm by NMR. We further show, using a combination of feeding studies and structure elucidation by NMR and high-resolution tandem mass spectrometry, that SBCb004 and An d48 together biosynthesize 22 additional tubulysin derivatives. These data reveal the inherently diversity-oriented nature of the tubulysin biosynthetic pathway.