N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine
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N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-003183
CAS number
261380-16-9
Molecular Formula
C12H16BrNO4S
Molecular Weight
350.23
N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine
IUPAC Name
(2R)-3-(5-bromothiophen-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Ala{2-Thienyl(5-Br)}-OH; Boc-D-Thi(2)(5-Br)-OH; BOC-D-2-(5-BROMOTHIENYL)ALANINE; (R)-3-(5-Bromothiophen-2-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid; N-TERT-BUTOXYCARBONYL-(5-BROMO-2-THIENYL)-D-ALANINE; Boc-3-(5-bromothien-2-yl)-D-alanine; (R)-N-BOC-2-(5-BROMOTHIENYL)ALANINE; Boc-D-2-(5-bromothienyl)alanine; Boc-D-α-(5-bromothienyl)alanine
Appearance
White powder
Purity
≥ 99% (HPLC,Chiral purity)
Density
1.494 g/cm3
Melting Point
83-89 °C
Boiling Point
473.8 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H16BrNO4S/c1-12(2,3)18-11(17)14-8(10(15)16)6-7-4-5-9(13)19-7/h4-5,8H,6H2,1-3H3,(H,14,17)(H,15,16)/t8-/m1/s1
InChI Key
HHNNFRCLMQFXBA-MRVPVSSYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC=C(S1)Br)C(=O)O

N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine, a chemical compound with diverse applications in peptide synthesis and research, plays a pivotal role in various domains. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: As a fundamental component in solid-phase peptide synthesis, this compound serves as a crucial building block. By safeguarding the amino group, it enables the sequential assembly of peptides mitigating undesired side reactions. This streamlined process facilitates the creation of intricate peptides with exceptional purity and specificity.

Drug Development: Within the realm of drug discovery, N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine finds relevance in crafting peptidomimetics synthetic compounds that mimic peptide structures and functions. These peptidomimetics have the potential to yield novel therapeutic agents. Notably the unique thienyl group offers specific interaction capabilities ideal for binding studies and innovative drug design endeavors.

Proteomics Research: In the realm of proteomics, this compound is utilized to generate modified peptides for mass spectrometry analyses. By incorporating N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine, researchers can accurately label and identify peptide fragments. This process aids in mapping protein sequences and decoding intricate protein functions advancing our understanding of proteomic landscapes.

Structural Biology: Capitalizing on its properties, N-α-(t-Butoxycarbonyl)-β-(5-bromo-2-thienyl)-D-alanine contributes to structural biology studies by facilitating the design of peptides with specific structural attributes. These tailored peptides play a vital role in elucidating protein-peptide interactions and unraveling protein folding mechanisms. Such insights are indispensable for fueling drug discovery initiatives and driving groundbreaking biochemical research forward.

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