Name: FMOC-L-HYP(BOM)-OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-(t-butyloxycarbonylaminoethylcarbamoyl)-trans-L-hydroxyproline; Fmoc-Hyp(Bcc)-OH; (4R)-1-Fmoc-4-[[[(2-Boc-amino-ethyl)amino]carbonyl]oxy]-L-proline

IUPAC Name

(2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylcarbamoyloxy]pyrrolidine-2-carboxylic acid

Canonical SMILES

CC(C)(C)OC(=O)NCCNC(=O)OC1CC(N(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O

InChI

InChI=1S/C28H33N3O8/c1-28(2,3)39-26(35)30-13-12-29-25(34)38-17-14-23(24(32)33)31(15-17)27(36)37-16-22-20-10-6-4-8-18(20)19-9-5-7-11-21(19)22/h4-11,17,22-23H,12-16H2,1-3H3,(H,29,34)(H,30,35)(H,32,33)/t17-,23+/m1/s1

InChIKey

PFVAFJSUWCTINJ-HXOBKFHXSA-N

Density

1.35±0.1 g/cm3

Appearance

White to Pink Solid

Quantity

Data not available, please inquire.

Boiling Point

749.0±60.0 °C at 760 mmHg

FMOC-L-HYP(BOM)-OH is a specialized amino acid derivative used extensively in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS). The FMOC (9-fluorenylmethyloxycarbonyl) group is a well-known protective group for the amino terminus of peptides. It allows for the controlled and sequential addition of amino acids while minimizing side reactions. FMOC-L-HYP(BOM)-OH contains hydroxyproline (HYP), a key amino acid found in collagen, which introduces specific structural and functional properties into peptides. This compound is essential in synthesizing peptides that mimic the structure of collagen or other proteins containing hydroxyproline.

The BOM (benzyl oxy methyl) group in FMOC-L-HYP(BOM)-OH is a protecting group for the hydroxyl functionality of hydroxyproline. This protection is crucial during peptide synthesis to prevent unwanted side reactions that could degrade the peptide chain. The BOM group can be selectively removed under mild conditions, typically using hydrogenation, which makes FMOC-L-HYP(BOM)-OH a versatile intermediate for peptides where controlled deprotection is necessary. The BOM group also contributes to the stability of the peptide during synthesis, allowing for more reliable outcomes in complex synthetic processes.

FMOC-L-HYP(BOM)-OH plays a significant role in the synthesis of collagen-like peptides, which are used in various fields such as biomedical research, drug development, and cosmetic formulations. Collagen mimetic peptides are designed to mimic the triple helix structure of natural collagen and are crucial for understanding collagen's role in tissue repair, skin regeneration, and wound healing. By incorporating hydroxyproline residues, FMOC-L-HYP(BOM)-OH helps produce peptides that closely resemble the natural collagen structure, offering insights into collagen-based therapies and biomaterial design.

Another important application of FMOC-L-HYP(BOM)-OH is in the creation of peptides with enhanced stability and bioactivity. Hydroxyproline-containing peptides are often more resistant to enzymatic degradation compared to standard peptides, making them suitable for therapeutic applications that require prolonged stability in biological environments. By using FMOC-L-HYP(BOM)-OH, researchers can synthesize peptides that have improved resistance to proteolysis, which is beneficial in the development of peptide-based drugs or biologics. This property is also valuable for studying peptide-receptor interactions and protein stability.